Natural products in synthesis and biosynthesis

Editor: Dr. Jeroen S. Dickschat
Technische Universität Braunschweig

This is the second Thematic Series in this journal focused on natural products. While the first series summarized recent research work on the biosynthesis and function of natural products, the present one deals with synthetic and biosynthetic aspects. Of course, the chemistry of nature and as it is used by chemists is one and the same and makes use of the same intrinsic reactivity of molecules. It is fascinating to see that a particular chemical reaction, believed to be invented by man, is in fact already used for millions of years by Mother Nature. An interesting example is the discovery of the Diels–Alder reaction in the 1920s and its later enhancement into an enantioselective reaction by the development of chiral catalysts. But a Diels–Alder reaction also occurs in the biosynthesis of lovastatin and is likely catalysed by a Diels–Alderase, a natural analogue of man-made chiral catalysts.

See also the Thematic Series:
Natural products in synthesis and biosynthesis II

See videos about natural products at Beilstein TV.

Natural products in synthesis and biosynthesis

Jeroen S. Dickschat

Editorial
Published 19 Sep 2013

PDF
Album
1. Figure 1: Calicheamycin.
  
  Jump to Figure 1

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 1897–1898, doi:10.3762/bjoc.9.223

Full Text

Total synthesis of ochnaflavone

Monica M. Ndoile and
Fanie R. van Heerden

Full Research Paper
Published 08 Jul 2013

PDF
Album
1. Graphical Abstract
2. Figure 1: Structure of ochnaflavone (1).
  
  Jump to Figure 1
3. Scheme 1: Synthesis of ochnaflavone (1).
  
  Jump to Scheme 1
4. Scheme 2: Oxalic acid-induced ring closure of bichalcone 6.
  
  Jump to Scheme 2

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 1346–1351, doi:10.3762/bjoc.9.152

Full Text

Synthesis and biological activities of the respiratory chain inhibitor aurachin D and new ring versus chain analogues

Xu-Wen Li,
Jennifer Herrmann,
Yi Zang,
Philippe Grellier,
Soizic Prado,
Rolf Müller and
Bastien Nay

Full Research Paper
Published 31 Jul 2013

PDF
Album
1. Graphical Abstract
2. Figure 1: The 2-methyl-4(1H)-quinolone compounds: aurachins and endochin.
  
  Jump to Figure 1
3. Scheme 1: Synthesis of aurachin D (4) and geranyl (9), prenyl (10) and methyl (11) analogues.
  
  Jump to Scheme 1
4. Scheme 2: Strategy toward the heterocyclic core of aurachin H.
  
  Jump to Scheme 2
5. Figure 2: (A) Loss of mitochondrial membrane potential in human U-2 OS osteosarcoma cells that were treated w...
  
  Jump to Figure 2
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 1551–1558, doi:10.3762/bjoc.9.176

Full Text

New tridecapeptides of the theonellapeptolide family from the Indonesian sponge Theonella swinhoei

Annamaria Sinisi,
Barbara Calcinai,
Carlo Cerrano,
Henny A. Dien,
Angela Zampella,
Claudio D’Amore,
Barbara Renga,
Stefano Fiorucci and
Orazio Taglialatela-Scafati

Full Research Paper
Published 13 Aug 2013

PDF
Album
1. Graphical Abstract
2. Figure 1: Structure of the known compound theonellapeptolide Id (1).
  
  Jump to Figure 1
3. Figure 2: Structures of sulfinyltheonellapeptolide (2) and theonellapeptolide If (3).
  
  Jump to Figure 2
4. Figure 3: COSY and key HMBC correlations (left) and MS/MS fragmentations of 2 and its ring-opened methanolysi...
  
  Jump to Figure 3
5. Figure 4: Antiproliferative activity of theonellapeptolides 1–3 on hepatic carcinoma cell line. The MTT assay...
  
  Jump to Figure 4
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 1643–1651, doi:10.3762/bjoc.9.188

Full Text

Synthesis of the reported structure of piperazirum using a nitro-Mannich reaction as the key stereochemical determining step

James C. Anderson,
Andreas S. Kalogirou,
Michael J. Porter and
Graham J. Tizzard

Letter
Published 23 Aug 2013

PDF
Album
1. Graphical Abstract
2. Scheme 1: Schematic nitro-Mannich reaction.
  
  Jump to Scheme 1
3. Scheme 2: Retrosynthetic analysis of piperazirum.
  
  Jump to Scheme 2
4. Scheme 3: (a) iBuMgCl, Et₂O, −78 °C; (b) KOH, EtOH/H₂O, 100 °C; (c) (COCl)₂.
  
  Jump to Scheme 3
5. Scheme 4: (a) Li(Et₃BH), THF, rt then 14, CF₃CO₂H, −78 °C, dr 70:30; (b) (CF₃CO)₂O, Py, CH₂Cl₂, 0 °C to rt; (...
  
  Jump to Scheme 4
6. Scheme 5: (a) Li(Et₃BH), CH₂Cl₂, rt then 19, CF₃CO₂H, −78 °C, dr >95:5; (b) Zn, 6 M HCl, EtOAc/EtOH, rt, sing...
  
  Jump to Scheme 5
7. Scheme 6: (a) (COCl)₂, DMF, CH₂Cl₂, rt; (b) 21, Py, DMAP, CH₂Cl₂, rt; (c) EDC, HOBt, THF/CH₂Cl₂, rt; (d) H₂ (...
  
  Jump to Scheme 6
8. Figure 1: X-ray crystal structure of 2·HCl.
  
  Jump to Figure 1
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 1737–1744, doi:10.3762/bjoc.9.200

Full Text

Activation of cryptic metabolite production through gene disruption: Dimethyl furan-2,4-dicarboxylate produced by Streptomyces sahachiroi

Dinesh Simkhada,
Huitu Zhang,
Shogo Mori,
Howard Williams and
Coran M. H. Watanabe

Letter
Published 29 Aug 2013

PDF
Album
1. Graphical Abstract
2. Figure 1: Schematic diagram illustrating the phenotypic effects arising through deletion of the aziA2 gene.
  
  Jump to Figure 1
3. Figure 2: HPLC profiles of (A) S. sahachiroi wild-type and (B) ΔaziA2 crude organic extracts.
  
  Jump to Figure 2
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 1768–1773, doi:10.3762/bjoc.9.205

Full Text

Synthesis and antibacterial activity of monocyclic 3-carboxamide tetramic acids

Yong-Chul Jeong and
Mark G. Moloney

Full Research Paper
Published 19 Sep 2013

PDF
Album
1. Graphical Abstract
2. Figure 1: Some antibiotic natural and unnatural tetramic acids.
  
  Jump to Figure 1
3. Scheme 1: Synthesis of simple 3-carboxamide tetramic acids. Reaction conditions: (a) triethylamine (2.0 equiv...
  
  Jump to Scheme 1
4. Scheme 2: Synthesis of N-alkyl 3-carboxamide tetramic acid. Reaction conditions: (a) 1. glycine methyl ester∙...
  
  Jump to Scheme 2
5. Scheme 3: Synthesis of C(5)-alkyl 3-carboxamide tetramic acids. Reaction conditions: (a) butyl chloroformate ...
  
  Jump to Scheme 3
6. Figure 2: Tautomerism of tetramates.
  
  Jump to Figure 2
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 1899–1906, doi:10.3762/bjoc.9.224

Full Text

Stereoselective synthesis of the C79–C97 fragment of symbiodinolide

Hiroyoshi Takamura,
Takayuki Fujiwara,
Isao Kadota and
Daisuke Uemura

Letter
Published 25 Sep 2013

PDF
Album
1. Graphical Abstract
2. Figure 1: Structure of symbiodinolide (1).
  
  Jump to Figure 1
3. Scheme 1: Our previous synthesis of the C79–C96 fragment 7.
  
  Jump to Scheme 1
4. Scheme 2: Retrosynthetic analysis of the C79–C97 fragment 8.
  
  Jump to Scheme 2
5. Scheme 3: Synthesis of aldehyde 20.
  
  Jump to Scheme 3
6. Scheme 4: Synthesis of PT-sulfones 23 and 24.
  
  Jump to Scheme 4
7. Scheme 5: Synthesis of the C79–C97 fragment 27.
  
  Jump to Scheme 5
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 1931–1935, doi:10.3762/bjoc.9.228

Full Text

A concise enantioselective synthesis of the guaiane sesquiterpene (−)-oxyphyllol

Martin Zahel and
Peter Metz

Full Research Paper
Published 08 Oct 2013

PDF
Album
1. Graphical Abstract
2. Figure 1: Structure of the guaiane (−)-oxyphyllol (1).
  
  Jump to Figure 1
3. Scheme 1: Retrosynthetic analysis for (−)-oxyphyllol (1) and structures of the guaiane sesquiterpenes (+)-ori...
  
  Jump to Scheme 1
4. Scheme 2: Attempted selective deoxygenation of diol 7. a) 1 mol % K₂OsO₄, NMO, acetone, water, THF, rt, 97%, ...
  
  Jump to Scheme 2
5. Scheme 3: Conversion of 4 to 1. a) 20 mol % Co(acac)₂, PhSiH₃, 1 atm O₂, THF, 0°C, 82%, diastereomeric ratio ...
  
  Jump to Scheme 3
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 2028–2032, doi:10.3762/bjoc.9.239

Full Text

The chemistry of isoindole natural products

Klaus Speck and
Thomas Magauer

Review
Published 10 Oct 2013

PDF
Album
1. Graphical Abstract
2. Figure 1: a) Structural features and b) selected examples of non-natural congeners.
  
  Jump to Figure 1
3. Scheme 1: Synthesis of isoindole 18.
  
  Jump to Scheme 1
4. Scheme 2: Staining amines with 1,4-diketone 19 (R = H).
  
  Jump to Scheme 2
5. Figure 2: Representative members of the indolocarbazole alkaloid family.
  
  Jump to Figure 2
6. Figure 3: Staurosporine (26) bound to the adenosine-binding pocket [19] (from pdb1stc).
  
  Jump to Figure 3
7. Figure 4: Structure of imatinib (34) and midostaurin (35).
  
  Jump to Figure 4
8. Scheme 3: Biosynthesis of staurosporine (26).
  
  Jump to Scheme 3
9. Scheme 4: Wood’s synthesis of K-252a via the common intermediate 48.
  
  Jump to Scheme 4
10. Scheme 5: Synthesis of 26, 27, 49 and 50 diverging from the common intermediate 48.
  
  Jump to Scheme 5
11. Figure 5: Selected members of the cytochalasan alkaloid family.
  
  Jump to Figure 5
12. Scheme 6: Biosynthesis of chaetoglobosin A (57) [56].
  
  Jump to Scheme 6
13. Scheme 7: Synthesis of cytochalasin D (70) by Thomas [63].
  
  Jump to Scheme 7
14. Scheme 8: Synthesis of L-696,474 (78).
  
  Jump to Scheme 8
15. Scheme 9: Synthesis of aldehyde 85 (R = TBDPS).
  
  Jump to Scheme 9
16. Scheme 10: Synthesis of (+)-aspergillin PZ (79) by Tanis.
  
  Jump to Scheme 10
17. Figure 6: Representative Berberis alkaloids.
  
  Jump to Figure 6
18. Scheme 11: Proposed biosynthetic pathway to chilenine (93).
  
  Jump to Scheme 11
19. Scheme 12: Synthesis of magallanesine (97) by Danishefsky [84].
  
  Jump to Scheme 12
20. Scheme 13: Kurihara’s synthesis of magallanesine (85).
  
  Jump to Scheme 13
21. Scheme 14: Proposed biosynthesis of 113, 117 and 125.
  
  Jump to Scheme 14
22. Scheme 15: DNA lesion caused by aristolochic acid I (117) [102].
  
  Jump to Scheme 15
23. Scheme 16: Snieckus’ synthesis of piperolactam C (131).
  
  Jump to Scheme 16
24. Scheme 17: Synthesis of aristolactam BII (104).
  
  Jump to Scheme 17
25. Figure 7: Representative cularine alkaloids.
  
  Jump to Figure 7
26. Scheme 18: Proposed biosynthesis of 136.
  
  Jump to Scheme 18
27. Scheme 19: The syntheses of 136 and 137 reported by Castedo and Suau.
  
  Jump to Scheme 19
28. Scheme 20: Synthesis of 136 by Couture.
  
  Jump to Scheme 20
29. Figure 8: Representative isoindolinone meroterpenoids.
  
  Jump to Figure 8
30. Scheme 21: Postulated biosynthetic pathway for the formation of 156 (adopted from George) [143].
  
  Jump to Scheme 21
31. Scheme 22: Synthesis of stachyflin (156) by Katoh [144].
  
  Jump to Scheme 22
32. Figure 9: Selected examples of spirodihydrobenzofuranlactams.
  
  Jump to Figure 9
33. Scheme 23: Synthesis of stachybotrylactam I (157).
  
  Jump to Scheme 23
34. Scheme 24: Synthesis of pestalachloride A (193) by Schmalz.
  
  Jump to Scheme 24
35. Scheme 25: Proposed mechanism for the BF₃-catalyzed metal-free carbonyl–olefin metathesis [149].
  
  Jump to Scheme 25
36. Scheme 26: Preparation of the isoindoline core of muironolide A (204).
  
  Jump to Scheme 26
37. Scheme 27: Proposed biosynthesis of 208.
  
  Jump to Scheme 27
38. Scheme 28: Model for the biosynthesis of 215 and 217.
  
  Jump to Scheme 28
39. Scheme 29: Synthesis of lactonamycin (215) and lactonamycin Z (217).
  
  Jump to Scheme 29
40. Figure 10: Hetisine alkaloids 225–228.
  
  Jump to Figure 10
41. Scheme 30: Biosynthetic proposal for the formation of the hetisine core [167].
  
  Jump to Scheme 30
42. Scheme 31: Synthesis of nominine (225).
  
  Jump to Scheme 31
Video

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 2048–2078, doi:10.3762/bjoc.9.243

Full Text

Flexible synthesis of anthracycline aglycone mimics via domino carbopalladation reactions

Markus Leibeling and
Daniel B. Werz

Full Research Paper
Published 24 Oct 2013

PDF
Album
1. Graphical Abstract
2. Figure 1: Several natural occurring anthracycline antibiotics.
  
  Jump to Figure 1
3. Scheme 1: Total synthesis of daunomycinone 6 according to Hansen.
  
  Jump to Scheme 1
4. Scheme 2: Synthesis of simplified anthracycline derivatives.
  
  Jump to Scheme 2
5. Scheme 3: Retrosynthetic analysis of anthracycline aglycone mimics. Si: any silyl group.
  
  Jump to Scheme 3
6. Scheme 4: Synthetic route for the synthesis of various dialkynes 16. ^aSi: TMS, SiMe₂Bn (2.0 equiv); Si: SiMe₂...
  
  Jump to Scheme 4
7. Scheme 5: Silyl ether synthesis and domino carbopalladation reaction. R,R (Glc): isopropylidene. R,R (Gal): b...
  
  Jump to Scheme 5
8. Scheme 6: Derivatisation of anthracycline derivatives. ^aR,R (Glc): isopropylidene. R,R (Gal): benzylidene. Re...
  
  Jump to Scheme 6
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 2194–2201, doi:10.3762/bjoc.9.258

Full Text

Synthesis and characterization of novel bioactive 1,2,4-oxadiazole natural product analogs bearing the N-phenylmaleimide and N-phenylsuccinimide moieties

Catalin V. Maftei,
Elena Fodor,
Peter G. Jones,
M. Heiko Franz,
Gerhard Kelter,
Heiner Fiebig and
Ion Neda

Full Research Paper
Published 25 Oct 2013

PDF
Album
1. Graphical Abstract
2. Figure 1: Natural products having a 1,2,4-oxadiazole core.
  
  Jump to Figure 1
3. Figure 2: Examples of 1,2,4-oxadiazole antitumorals.
  
  Jump to Figure 2
4. Scheme 1: Common synthetic strategies toward 1,2,4-oxadiazoles; (a) amidoxime route; (b) 1,3 dipolar cycloadd...
  
  Jump to Scheme 1
5. Scheme 2: One-pot synthesis of 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)aniline (1) by using the amidoxime route....
  
  Jump to Scheme 2
6. Figure 3: Molecular structure of 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)aniline (1). Atoms are drawn as 50% the...
  
  Jump to Figure 3
7. Figure 4: Packing diagram of compound 1. Hydrogen bonds are indicated as dashed lines.
  
  Jump to Figure 4
8. Scheme 3: One-pot synthesis of 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)aniline (1) by using the 1,3-dipolar cycl...
  
  Jump to Scheme 3
9. Figure 5: Molecular structure of 3-tert-butyl-5-(4-nitrophenyl)-1,2,4-oxadiazole (2). Atoms are drawn as 50% ...
  
  Jump to Figure 5
10. Figure 6: Packing diagram of compound (2) showing C–H···O interactions.
  
  Jump to Figure 6
11. Scheme 4: Synthesis of 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)pyrrolidine-2,5-dione (4).
  
  Jump to Scheme 4
12. Figure 7: Molecular structure of 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)pyrrolidine-2,5-dione (4). At...
  
  Jump to Figure 7
13. Figure 8: Molecular structure of 4-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylamino)-4 oxobutanoate (5). Ato...
  
  Jump to Figure 8
14. Figure 9: Packing diagram of compound (5). Dashed lines indicate hydrogen bonds.
  
  Jump to Figure 9
15. Scheme 5: Synthesis of 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)-1H-pyrrole-2,5-dione (7).
  
  Jump to Scheme 5
16. Figure 10: Molecular structure of (Z)-4-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylamino)-4-oxobut-2-enoic ac...
  
  Jump to Figure 10
17. Figure 11: Packing diagram of compound 6. Dashed lines indicate hydrogen bonds.
  
  Jump to Figure 11
18. Figure 12: In vitro antitumor activity of compounds 1, 3–7 toward 11 human tumor cell lines.
  
  Jump to Figure 12
19. Figure 13: Individual IC₅₀ values [µM] of compounds 1, 3–7 in a panel of 11 human tumor cell lines.
  
  Jump to Figure 13

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 2202–2215, doi:10.3762/bjoc.9.259

Full Text

Elucidation of the regio- and chemoselectivity of enzymatic allylic oxidations with Pleurotus sapidus – conversion of selected spirocyclic terpenoids and computational analysis

Verena Weidmann,
Mathias Schaffrath,
Holger Zorn,
Julia Rehbein and
Wolfgang Maison

Full Research Paper
Published 29 Oct 2013

PDF
Album
1. Graphical Abstract
2. Figure 1: Selected biocatalytic allylic and benzylic oxidations with the lyophilisate of Pleurotus sapidus (P...
  
  Jump to Figure 1
3. Scheme 1: Biocatalytic allylic oxidation of theaspirane (1) with lyophilisates of PSA. Only one enantiomer of...
  
  Jump to Scheme 1
4. Figure 2: Selected bioactive terpenoids based on spiroether backbones [38,39].
  
  Jump to Figure 2
5. Scheme 2: Intramolecular silyl modified Sakurai reaction to spiroethers 7–9 and 11–13.
  
  Jump to Scheme 2
6. Scheme 3: Biocatalytic allylic oxidation of spiroethers 7, 8, 11 and 12 with the lyophilisate of PSA. Convers...
  
  Jump to Scheme 3
7. Figure 3: Bond-dissociation enthalpies for three allylic C–H bonds in 11. Double stabilization of the radical...
  
  Jump to Figure 3
8. Scheme 4: Improved 3-step synthesis of vitispirane (23) from theaspirane (1). Only one enantiomer of racemic ...
  
  Jump to Scheme 4
9. Scheme 5: Oxidation of vitispirane (23) with PSA gave enone 24 and two diastereomeric allyl alcohols 26a and ...
  
  Jump to Scheme 5
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 2233–2241, doi:10.3762/bjoc.9.262

Full Text

Cyclopamine analogs bearing exocyclic methylenes are highly potent and acid-stable inhibitors of hedgehog signaling

Johann Moschner,
Anna Chentsova,
Nicole Eilert,
Irene Rovardi,
Philipp Heretsch and
Athanassios Giannis

Full Research Paper
Published 31 Oct 2013

PDF
Album
1. Graphical Abstract
2. Figure 1: Structures of cyclopamine and exo-cyclopamine.
  
  Jump to Figure 1
3. Scheme 1: Synthesis of 25-epi-exo-cyclopamine 5, bis-exo-cyclopamine 6, and derivatives 8 and 9. Reaction con...
  
  Jump to Scheme 1
4. Scheme 2: Synthesis of 20-demethyl-bis-exo-cyclopamine 19 and F-nor-20,25-bis-demethyl-exo-cyclopamine 23. Re...
  
  Jump to Scheme 2
5. Figure 2: IC₅₀ values of Shh inhibition by compounds 5, 6 and 23 in a Gli1-reporter gene assay. Data were obt...
  
  Jump to Figure 2
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 2328–2335, doi:10.3762/bjoc.9.267

Full Text

Towards stereochemical control: A short formal enantioselective total synthesis of pumiliotoxins 251D and 237A

Jie Zhang,
Hong-Kui Zhang and
Pei-Qiang Huang

Full Research Paper
Published 05 Nov 2013

PDF
Album
1. Graphical Abstract
2. Figure 1: Structures of some pumiliotoxins and an advanced intermediate.
  
  Jump to Figure 1
3. Scheme 1: Synthesis of 5 from 6 via oxidation–addition sequence.
  
  Jump to Scheme 1
4. Scheme 2: Plausible stereochemical course of the preferential axial addition of methylmagnesium iodide to bic...
  
  Jump to Scheme 2
5. Scheme 3: Holmes’ exclusive trans-diastereoselective methylation of N-Cbz-protected piperidin-3-one 8.
  
  Jump to Scheme 3
6. Scheme 4: Our plan for the trans-diastereoselective methylation of keto-lactam 10.
  
  Jump to Scheme 4
7. Scheme 5: Retrosynthetic analysis of (8S,8aS)-8-hydroxy-8-methylindolizidin-5-one (5).
  
  Jump to Scheme 5
8. Scheme 6: Synthesis of compound 18.
  
  Jump to Scheme 6
9. Scheme 7: Synthesis of hydroxylactam 18.
  
  Jump to Scheme 7
10. Scheme 8: Synthesis of tertiary alcohol 22.
  
  Jump to Scheme 8
11. Scheme 9: Synthesis of (8S,8aS)-5 and its silyl ether 23.
  
  Jump to Scheme 9
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 2358–2366, doi:10.3762/bjoc.9.271

Full Text

A protecting group-free synthesis of the Colorado potato beetle pheromone

Zhongtao Wu,
Manuel Jäger,
Jeffrey Buter and
Adriaan J. Minnaard

Letter
Published 06 Nov 2013

PDF
Album
1. Graphical Abstract
2. Figure 1: (S)-1,3-dihydroxy-3,7-dimethyl-6-octen-2-one (1).
  
  Jump to Figure 1
3. Scheme 1: Selective oxidation of glycerol [15] and methyl α-D-glucopyranoside.
  
  Jump to Scheme 1
4. Scheme 2: Approach of synthesis of (S)-1.
  
  Jump to Scheme 2
5. Scheme 3: Synthesis of (S)-1 from geraniol. Reagents and conditions: a) D-(−)-diisopropyl tartrate, Ti(OiPr)₄...
  
  Jump to Scheme 3
6. Scheme 4: Synthesis starting from nerol. Reagents and conditions: a) L-(+)-diisopropyl tartrate, Ti(OiPr)₄, t...
  
  Jump to Scheme 4
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 2374–2377, doi:10.3762/bjoc.9.273

Full Text

Biosynthesis of rare hexoses using microorganisms and related enzymes

Zijie Li,
Yahui Gao,
Hideki Nakanishi,
Xiaodong Gao and
Li Cai

Review
Published 12 Nov 2013

PDF
Album
1. Graphical Abstract
2. Scheme 1: Synthesis of D-tagatose from D-galactose using L-arabinose isomerase.
  
  Jump to Scheme 1
3. Scheme 2: Synthesis of D-psicose from D-fructose using D-tagatose 3-epimerase/D-psicose 3-epimerase.
  
  Jump to Scheme 2
4. Figure 1: The active site in D-psicose 3-epimerase (DPEase) in the presence of D-fructose, showing the metal ...
  
  Jump to Figure 1
5. Scheme 3: Enzymatic synthesis of D-psicose using aldolase FucA.
  
  Jump to Scheme 3
6. Scheme 4: Proposed pathway of the D-sorbose synthesis from galactitol or L-glucitol.
  
  Jump to Scheme 4
7. Scheme 5: Simultaneous enzymatic synthesis of D-sorbose and D-psicose.
  
  Jump to Scheme 5
8. Scheme 6: Biosynthesis of L-tagatose.
  
  Jump to Scheme 6
9. Scheme 7: Preparative-scale synthesis of L-tagatose and L-fructose using aldolase.
  
  Jump to Scheme 7
10. Scheme 8: Biosynthesis of L-fructose.
  
  Jump to Scheme 8
11. Scheme 9: Preparative-scale synthesis of L-fructose using aldolase RhaD.
  
  Jump to Scheme 9
12. Scheme 10: Chemoenzymatically synthesis of 1-deoxy-L-fructose [8].
  
  Jump to Scheme 10
13. Scheme 11: Potential enzymes (isomerases) for the bioconversion of D-psicose to D-allose.
  
  Jump to Scheme 11
14. Scheme 12: Three-step bioconversion of D-glucose to D-allose.
  
  Jump to Scheme 12
15. Scheme 13: Biosynthesis of L-glucose.
  
  Jump to Scheme 13
16. Scheme 14: Enzymatic synthesis of L-talose and D-gulose.
  
  Jump to Scheme 14
17. Scheme 15: Enzymatic synthesis of L-galactose.
  
  Jump to Scheme 15
18. Scheme 16: Enzymatic synthesis of L-fucose.
  
  Jump to Scheme 16
19. Scheme 17: Synthesis of allitol from D-fructose using a multi-enzyme system.
  
  Jump to Scheme 17
20. Scheme 18: Biosynthesis of D-talitol via C-2 reduction of rare sugars.
  
  Jump to Scheme 18
21. Scheme 19: Biosynthesis of L-sorbitol via C-2 reduction of rare sugars.
  
  Jump to Scheme 19

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 2434–2445, doi:10.3762/bjoc.9.281

Full Text

Synthesis of the spiroketal core of integramycin

Evgeny. V. Prusov

Letter
Published 12 Nov 2013

PDF
Album
1. Graphical Abstract
2. Figure 1: Structure of integramycin (1) and its producing organism, Actinoplanes sp. (Photo: J. Wink, HZI, Mi...
  
  Jump to Figure 1
3. Figure 2: Retrosynthetic analysis of integramycin.
  
  Jump to Figure 2
4. Scheme 1: Synthesis of the aromatic subunit.
  
  Jump to Scheme 1
5. Scheme 2: Sharpless epoxidation/Myers alkylation approach to the C16–C22 carboxylic acid fragment.
  
  Jump to Scheme 2
6. Scheme 3: Coupling of the fragments and spiroketalization.
  
  Jump to Scheme 3
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 2446–2450, doi:10.3762/bjoc.9.282

Full Text

Bidirectional cross metathesis and ring-closing metathesis/ring opening of a C₂-symmetric building block: a strategy for the synthesis of decanolide natural products

Bernd Schmidt and
Oliver Kunz

Full Research Paper
Published 18 Nov 2013

PDF
Album
1. Graphical Abstract
2. Scheme 1: RCM/base-induced ring-opening sequence.
  
  Jump to Scheme 1
3. Figure 1: Structures and numbering scheme for stagonolide E and curvulide A.
  
  Jump to Figure 1
4. Scheme 2: Synthetic plan for stagonolide E.
  
  Jump to Scheme 2
5. Scheme 3: Synthesis of RCM/ring opening precursor 14.
  
  Jump to Scheme 3
6. Scheme 4: Synthesis of a substrate 19 for “late stage” resolution.
  
  Jump to Scheme 4
7. Scheme 5: Synthesis of substrate 21 for “early stage” resolution.
  
  Jump to Scheme 5
8. Scheme 6: Synthesis of macrolactonization precursor 29.
  
  Jump to Scheme 6
9. Scheme 7: Synthesis of (2Z,4E)-9-hydroxy-2,4-dienoic acid (33) and its macrolactonization.
  
  Jump to Scheme 7
10. Scheme 8: Synthesis of published structure of fusanolide A (36).
  
  Jump to Scheme 8
11. Scheme 9: Completion of stagonolide E synthesis.
  
  Jump to Scheme 9
12. Scheme 10: Transition-state models for the Sharpless epoxidation of stagonolide E with L-(+)-DET (left) and D-...
  
  Jump to Scheme 10
13. Scheme 11: Synthesis of 39b (curvulide A) from stagonolide E.
  
  Jump to Scheme 11
14. Figure 2: MM2 energy-minimized structures of 39a and 39b.
  
  Jump to Figure 2
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 2544–2555, doi:10.3762/bjoc.9.289

Full Text

The regulation and biosynthesis of antimycins

Ryan F. Seipke and
Matthew I. Hutchings

Review
Published 19 Nov 2013

PDF
Album
1. Graphical Abstract
2. Figure 1: Antimycins: Antimycins A₁, A₂, A₃, and A₄ and non-natural antimycins referenced in the text. Antimy...
  
  Jump to Figure 1
3. Figure 2: Schematic representation of ant biosynthetic gene clusters. L-form ant gene clusters are encoded by...
  
  Jump to Figure 2
4. Figure 3: Proposed biosynthetic pathway for antimycins. The antimycin biosynthetic pathway is described in de...
  
  Jump to Figure 3
5. Figure 4: σ^AntA comprises a new subfamily of ECF RNA polymerase σ factors. σ^AntA amino acid sequences were al...
  
  Jump to Figure 4

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 2556–2563, doi:10.3762/bjoc.9.290

Full Text

Stereodivergent synthesis of jaspine B and its isomers using a carbohydrate-derived alkoxyallene as C₃-building block

Volker M. Schmiedel,
Stefano Stefani and
Hans-Ulrich Reissig

Full Research Paper
Published 19 Nov 2013

PDF
Album
1. Graphical Abstract
2. Scheme 1: Structure of jaspine B 1 and its stereoisomers 2–4.
  
  Jump to Scheme 1
3. Scheme 2: Retrosynthetic analysis of jaspine B leading to pentadecanal and an alkoxyallene.
  
  Jump to Scheme 2
4. Scheme 3: Synthesis of racemic dihydrofuran 8.
  
  Jump to Scheme 3
5. Scheme 4: Synthesis of racemic jaspine B rac-1 and its diastereomer rac-2.
  
  Jump to Scheme 4
6. Scheme 5: Synthesis of dihydrofurans 14 and 15.
  
  Jump to Scheme 5
7. Scheme 6: Synthesis of jaspine B (1) and its (2S,3R,4R)-diastereomer 2.
  
  Jump to Scheme 6
8. Scheme 7: Protection and separation of the diastereomers.
  
  Jump to Scheme 7
9. Scheme 8: Reduction of the separated diastereomers leading to jaspine B (1) and its diastereomer 2.
  
  Jump to Scheme 8
10. Scheme 9: Route to ent-jaspine B (3) and the (2R,3S,4S)-diastereomer 4.
  
  Jump to Scheme 9
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 2564–2569, doi:10.3762/bjoc.9.291

Full Text

The myxocoumarins A and B from Stigmatella aurantiaca strain MYX-030

Tobias A. M. Gulder,
Snežana Neff,
Traugott Schüz,
Tammo Winkler,
René Gees and
Bettina Böhlendorf

Full Research Paper
Published 20 Nov 2013

PDF
Album
1. Graphical Abstract
2. Figure 1: Structures of epothilone A (1), soraphen A_1α (2), pyrrolnitrin (3), fenpiclonil (4), myxothiazol A (...
  
  Jump to Figure 1
3. Figure 2: HMBC interactions used for the structure elucidation of myxocoumarin A (7).
  
  Jump to Figure 2
4. Figure 3: Chemical structure of myxocoumarin B (9).
  
  Jump to Figure 3
5. Scheme 1: Postulated biosynthetic pathway to myxocoumarins A (7) and B (9).
  
  Jump to Scheme 1
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 2579–2585, doi:10.3762/bjoc.9.293

Full Text

Garner’s aldehyde as a versatile intermediate in the synthesis of enantiopure natural products

Mikko Passiniemi and
Ari M.P. Koskinen

Review
Published 26 Nov 2013

PDF
Album
1. Graphical Abstract
2. Figure 1: Structures of limonene, carvone and thalidomide.
  
  Jump to Figure 1
3. Figure 2: Structure of Garner’s aldehyde.
  
  Jump to Figure 2
4. Scheme 1: (a) i) Boc₂O, 1.0 N NaOH (pH >10), dioxane, +5 °C → rt; ii) MeI, K₂CO₃, DMF, 0 °C → rt (86% over tw...
  
  Jump to Scheme 1
5. Scheme 2: (a) AcCl, MeOH, 0 °C → reflux (99%); (b) i) (Boc)₂O, Et₃N, THF, 0 °C → rt → 50 °C (89%); ii) Me₂C(O...
  
  Jump to Scheme 2
6. Scheme 3: (a) LiAlH₄, THF, rt (93–96%); (b) (COCl)₂, DMSO, iPr₂NEt, CH₂Cl₂, −78 °C → −55 °C (99%).
  
  Jump to Scheme 3
7. Scheme 4: The Koskinen procedure for the preparation of Garner’s aldehyde. (a) i) AcCl, MeOH, 0 °C → 50 °C (9...
  
  Jump to Scheme 4
8. Scheme 5: Burke’s synthesis of Garner’s aldehyde. BDP - bis(diazaphospholane).
  
  Jump to Scheme 5
9. Figure 3: Structures of some iminosugars (7, 9), peptide antibiotics (8) and sphingosine (10) and pachastriss...
  
  Jump to Figure 3
10. Scheme 6: Use of Garner’s aldehyde 1 in multistep synthesis.
  
  Jump to Scheme 6
11. Scheme 7: Explanation of the anti- and syn-selectivity in the nucleophilic addition reaction.
  
  Jump to Scheme 7
12. Scheme 8: Herold’s method: (a) Lithium 1-pentadecyne, HMPT, THF, −78 °C (71%); (b) Lithium 1-pentadecyne, ZnBr...
  
  Jump to Scheme 8
13. Scheme 9: (a) Ethyl lithiumpropiolate, HMPT, THF, −78 °C; (b) (S)- or (R)-MTPA, DCC, DMAP, THF, rt (18, 81%) ...
  
  Jump to Scheme 9
14. Scheme 10: Coleman’s selectivity studies and their transition state model for the co-ordinated delivery of the...
  
  Jump to Scheme 10
15. Scheme 11: (a) PhMgBr, THF, −78 °C → 0 °C [62] or (a) PhMgBr, Et₂O, 0 °C [63].
  
  Jump to Scheme 11
16. Scheme 12: (a) cat. RhCl₃·3H₂O, cat. 26, NaOMe, Ph-B(OH)₂, aq DME, 80 °C (24, 71%); (b) cat. RhCl₃·3H₂O, cat. ...
  
  Jump to Scheme 12
17. Scheme 13: Lithiated dithiane (3 equiv), CuI (0.3 equiv), BF₃·Et₂O (6 equiv), THF, −50 °C, 12 h (70%).
  
  Jump to Scheme 13
18. Scheme 14: Addition reaction reported by Lam et al. (a) 1-Hexyne, n-BuLi, THF, −15 °C or −40 °C.
  
  Jump to Scheme 14
19. Scheme 15: (a) n-BuLi, HMPT, toluene, −78 °C → rt (85%); (b) n-BuLi, ZnCl₂, toluene/Et₂O, −78 °C → rt (65%).
  
  Jump to Scheme 15
20. Scheme 16: (a) n-BuLi, 34, THF, −40 °C [69]; (b) n-BuLi, 35, THF, −78 °C → rt (80%) [70]; (c) n-BuLi, 35, HMPT, THF, −...
  
  Jump to Scheme 16
21. Scheme 17: (a) cat. Rh(acac)(CO)₂, 42, THF, 40 °C (74%).
  
  Jump to Scheme 17
22. Scheme 18: (a) 1-PropynylMgBr, CuI, THF, Me₂S, −78 °C (95%); (b) Ethynyltrimethylsilane, EtMgBr, CuI, THF, Me₂...
  
  Jump to Scheme 18
23. Scheme 19: (a) cat. 50, toluene, 0 °C (52%); (b) cat. 51, toluene, 0 °C (51%); (c) cat. 52, toluene, 0 °C (50%...
  
  Jump to Scheme 19
24. Scheme 20: (a) (iPr)₃SiH, cat. Ni(COD)₂, dimesityleneimidazolium·HCl, t-BuOK, THF, rt.
  
  Jump to Scheme 20
25. Scheme 21: (a) Cp₂Zr(H)Cl, cat. AgAsF₆, CH₂Cl₂, rt; (b) Cp₂Zr(H)Cl, 1-pentadecyne, cat. ZnBr₂ in THF for anti-...
  
  Jump to Scheme 21
26. Scheme 22: (a) i) 31, n-BuLi, THF, −78 °C; ii) (S)-1, THF, −78 °C; (b) Red-Al, THF, 0 °C.
  
  Jump to Scheme 22
27. Scheme 23: (a) 61, n-BuLi, DMPU, toluene, −78 °C, then (S)-1, toluene, −95 °C (57%); (b) 61, n-BuLi, ZnCl₂, to...
  
  Jump to Scheme 23
28. Scheme 24: Olefin A as an intermediate in natural product synthesis.
  
  Jump to Scheme 24
29. Scheme 25: (a) Ph₃(Me)PBr, KH, benzene (66%, rac-64) or (b) AlMe₃, Zn, CH₂I₂, THF (76%) [101]; (c) Ph₃(Me)PBr, n-Bu...
  
  Jump to Scheme 25
30. Scheme 26: (a) Benzene, rt (82%) [108]; (b) K₂CO₃, MeOH (85%) [89]; (c) iPrOH, [Ir(COD)Cl]₂, PPh₃, THF, rt (81%) [114].
  
  Jump to Scheme 26
31. Scheme 27: Mechanism of the Still–Gennari modification of the HWE reaction leading to both olefin isomers.
  
  Jump to Scheme 27

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 2641–2659, doi:10.3762/bjoc.9.300

Full Text

Halogenated volatiles from the fungus Geniculosporium and the actinomycete Streptomyces chartreusis

Tao Wang,
Patrick Rabe,
Christian A. Citron and
Jeroen S. Dickschat

Full Research Paper
Published 03 Dec 2013

PDF
Album
1. Graphical Abstract
2. Figure 1: Total ion chromatogram of a CLSA headspace extract from Geniculosporium.
  
  Jump to Figure 1
3. Figure 2: Mass spectra of A) the chlorinated volatile X and B) the chlorinated volatile Y.
  
  Jump to Figure 2
4. Figure 3: Constitutional isomers of chlorodimethoxybenzene as candidate structures for X.
  
  Jump to Figure 3
5. Scheme 1: Synthesis of chlorodimethoxybenzenes as reference compounds for X.
  
  Jump to Scheme 1
6. Figure 4: Constitutional isomers of dichlorodimethoxybenzene as candidate structures for Y.
  
  Jump to Figure 4
7. Scheme 2: Synthesis of chlorodimethoxybenzenes as reference compounds for Y.
  
  Jump to Scheme 2
8. Figure 5: Known natural products that are structurally related to 4b and 10b from Geniculosporium.
  
  Jump to Figure 5
9. Figure 6: Total ion chromatograms of headspace extracts from S. chartreusis. A) Growth on 84 GYM showing prod...
  
  Jump to Figure 6
10. Figure 7: Calicheamicin, a known iodinated compound from the actinomycete Micromonspora echinospora.
  
  Jump to Figure 7
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 2767–2777, doi:10.3762/bjoc.9.311

Full Text

[²H₂₆]-1-epi-Cubenol, a completely deuterated natural product from Streptomyces griseus

Christian A. Citron and
Jeroen S. Dickschat

Full Research Paper
Published 10 Dec 2013

PDF
Album
1. Graphical Abstract
2. Figure 1: Terpenoids from Streptomyces griseus.
  
  Jump to Figure 1
3. Figure 2: Total ion chromatograms of CLSA headspace extracts from S. griseus obtained after (A) incubation on...
  
  Jump to Figure 2
4. Figure 3: Mass spectra of 1-epi-cubenol. (A) Mass spectrum of natural 3 obtained after growth on 65.GYM; (B) ...
  
  Jump to Figure 3
5. Figure 4: Ion chromatograms of fully deuterated 3 for (A) the molecular ion (m/z = 248, 247, and 246), and (B...
  
  Jump to Figure 4

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 2841–2845, doi:10.3762/bjoc.9.319

Full Text

SF002-96-1, a new drimane sesquiterpene lactone from an Aspergillus species, inhibits survivin expression

Silke Felix,
Louis P. Sandjo,
Till Opatz and
Gerhard Erkel

Full Research Paper
Published 13 Dec 2013

PDF
Album
1. Graphical Abstract
2. Figure 1: Structure of SF002-96-1.
  
  Jump to Figure 1
3. Figure 2: COSY (bold) and HMBC (arrow) correlations of SF002-96-1.
  
  Jump to Figure 2
4. Figure 3: NOESY correlations of SF002-96-1.
  
  Jump to Figure 3
5. Figure 4: Effect of SF002-96-1 on survivin promoter activity, survivin mRNA levels and expression. (A) Colo 3...
  
  Jump to Figure 4
6. Figure 5: Effect of SF002-96-1 on Sat3 and NF-κB binding to the survivin promoter in Colo 320 cells analyzed ...
  
  Jump to Figure 5
7. Figure 6: SF002-96-1 induces apoptosis of Colo 320 cells. (A) Colo 320 cells were treated without (control) o...
  
  Jump to Figure 6
8. Figure 7: Single-quadrupole mass spectrumof SF002-96-1 obtained using an atmospheric pressure chemical ioniza...
  
  Jump to Figure 7
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 2866–2876, doi:10.3762/bjoc.9.323

Full Text

Studies toward bivalent κ opioids derived from salvinorin A: heteromethylation of the furan ring reduces affinity

Thomas A. Munro,
Wei Xu,
Douglas M. Ho,
Lee-Yuan Liu-Chen and
Bruce M. Cohen

Full Research Paper
Published 20 Dec 2013

PDF
Album
1. Graphical Abstract
2. Figure 1: Binding affinities of salvinorin A (1) and furan derivatives for κ-OR [5].
  
  Jump to Figure 1
3. Figure 2: Crystal structure of κ-OR in complex with JDTic compared to naltrindole’s binding pose in δ-OR. A: ...
  
  Jump to Figure 2
4. Figure 3: Previously reported N-furanylalkyl opioid antagonists [19,20].
  
  Jump to Figure 3
5. Scheme 1: Syntheses of heteromethylated derivatives of 1. b.r.s.m. = based on recovered starting material.
  
  Jump to Scheme 1
6. Scheme 2: Synthesis of (2-hydroxyethoxy)methyl ether 6.
  
  Jump to Scheme 2
7. Figure 4: Crystal structure of 2 with 50% probability thermal displacement ellipsoids (cross-eyed stereoview)...
  
  Jump to Figure 4
8. Figure 5: Key ¹H–¹³C HMBC correlations.
  
  Jump to Figure 5
9. Figure 6: Known low-affinity derivatives of 1 screened in addition to 2–5 for negative allosteric modulation ...
  
  Jump to Figure 6
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 2916–2924, doi:10.3762/bjoc.9.328

Full Text

Synthesis and determination of the absolute configuration of (−)-(5R,6Z)-dendrolasin-5-acetate from the nudibranch Hypselodoris jacksoni

I. Wayan Mudianta,
Victoria L. Challinor,
Anne E. Winters,
Karen L. Cheney,
James J. De Voss and
Mary J. Garson

Full Research Paper
Published 23 Dec 2013

PDF
Album
1. Graphical Abstract
2. Figure 1: (−)-(5R,6Z)-Dendrolasin-5-acetate (1), its 6E derivative and naturally occuring dentrolasin (3).
  
  Jump to Figure 1
3. Figure 2: Selected HMBC, COSY, and nOe correlations of 1.
  
  Jump to Figure 2
4. Scheme 1: Synthetic route to sesquiterpene 1.
  
  Jump to Scheme 1
5. Scheme 2: Mechanism of Wittig rearrangement [21].
  
  Jump to Scheme 2
6. Figure 3: (a) NP HPLC trace showing separation of racemic 5-hydroxydendrolasin (7a/b) using hexanes/EtOAc (90...
  
  Jump to Figure 3
7. Figure 4: Analytical enantioselective HPLC trace showing separation of individual enantiomers of (6Z)-5-hydro...
  
  Jump to Figure 4
8. Figure 5: The ¹H NMR (CDCl₃, 500 MHz) spectroscopic comparison of (6Z)-dendrolasin-5-acetate (1): (a) sample ...
  
  Jump to Figure 5
9. Figure 6: RP HPLC trace showing separation of the MPA esters (R,R)-11 and (R,S)-11 (MeCN/H₂O, 63:35 over 50 m...
  
  Jump to Figure 6
10. Figure 7: Enantioselective HPLC profiles (5% isopropanol in n-hexane) of 1: (a) synthetic (±) mixture; (b) sy...
  
  Jump to Figure 7
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 2925–2933, doi:10.3762/bjoc.9.329

Full Text

Synthesis of novel derivatives of 5-hydroxymethylcytosine and 5-formylcytosine as tools for epigenetics

Anna Chentsova,
Era Kapourani and
Athanassios Giannis

Full Research Paper
Published 03 Jan 2014

PDF
Album
1. Graphical Abstract
2. Scheme 1: Proposed steps for DNA demethylation (for details see text).
  
  Jump to Scheme 1
3. Figure 1: Structures of the synthesized compounds.
  
  Jump to Figure 1
4. Scheme 2: Synthesis of the 2'-deoxycytidine analogues.
  
  Jump to Scheme 2
5. Scheme 3: Reactions of TCBoc-protected aldehydes 4 and 5 with organometallic reagents.
  
  Jump to Scheme 3
6. Scheme 4: Proposed mechanism for the formation of 3,6-dihydrodeoxycytidine derivatives 8a–d (M = Li, Mg).
  
  Jump to Scheme 4
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 7–11, doi:10.3762/bjoc.10.2

Full Text

Total synthesis of (+)-grandiamide D, dasyclamide and gigantamide A from a Baylis–Hillman adduct: A unified biomimetic approach

Andivelu Ilangovan and
Shanmugasundar Saravanakumar

Full Research Paper
Published 10 Jan 2014

PDF
Album
1. Graphical Abstract
2. Figure 1: Bisamides as building blocks for flavaglins.
  
  Jump to Figure 1
3. Figure 2: (+)-Grandiamide D, gigantamide A and dasyclamide.
  
  Jump to Figure 2
4. Scheme 1: Retrosynthetic analysis: A unified synthetic approach for the synthesis of grandiamide D, dasyclami...
  
  Jump to Scheme 1
5. Scheme 2: Preparation of N-(4-aminobutyl)cinnamamide.
  
  Jump to Scheme 2
6. Scheme 3: Synthesis of (±)-grandiamide D.
  
  Jump to Scheme 3
7. Scheme 4: Asymmetric synthesis of natural (+)-grandiamide D.
  
  Jump to Scheme 4
8. Scheme 5: Various approaches for the synthesis of (E)-N-(4-cinnamamidobutyl)-4-((4-methoxybenzyl)oxy)-2-methy...
  
  Jump to Scheme 5
9. Scheme 6: Synthesis of dasyclamide.
  
  Jump to Scheme 6
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 127–133, doi:10.3762/bjoc.10.9

Full Text

Physalin H from Solanum nigrum as an Hh signaling inhibitor blocks GLI1–DNA-complex formation

Midori A. Arai,
Kyoko Uchida,
Samir K. Sadhu,
Firoj Ahmed and
Masami Ishibashi

Full Research Paper
Published 13 Jan 2014

PDF
Album
1. Graphical Abstract
2. Figure 1: Schematic procedure of the constructed assay system; Tc (tetracycline), TetR (tetracycline represso...
  
  Jump to Figure 1
3. Figure 2: Isolated compounds from Solanum nigrum.
  
  Jump to Figure 2
4. Figure 3: GLI1 transcriptional activity and cytotoxicity. Reporter activity (solid columns) and cell viabilit...
  
  Jump to Figure 3
5. Figure 4: Inhibition of protein expression by compound 1. (A) Western blot analysis of PTCH, BCL-2 protein le...
  
  Jump to Figure 4
6. Figure 5: Inhibitory activity of GLI1–DNA-complex formation by electron mobility shift assay (EMSA). GST–GLI1...
  
  Jump to Figure 5

Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 134–140, doi:10.3762/bjoc.10.10

Full Text

Recent applications of the divinylcyclopropane–cycloheptadiene rearrangement in organic synthesis

Sebastian Krüger and
Tanja Gaich

Review
Published 16 Jan 2014

PDF
Album
1. Graphical Abstract
2. Scheme 1: Vogel’s first approach towards the divinylcyclopropane rearrangement [4] and characterization of cis-d...
  
  Jump to Scheme 1
3. Scheme 2: Transition states for the Cope rearrangement and the related DVCPR. Ts = transition state.
  
  Jump to Scheme 2
4. Scheme 3: Two possible mechanisms of trans-cis isomerizations of divinylcyclopropanes.
  
  Jump to Scheme 3
5. Scheme 4: Proposed biosynthesic pathway to ectocarpene (21), an inactive degradation product of a sexual pher...
  
  Jump to Scheme 4
6. Scheme 5: Proposed biosynthesis of occidenol (25) and related natural compounds.
  
  Jump to Scheme 5
7. Scheme 6: Gaich’s bioinspired system using the DVCPR to mimick the dimethylallyltryptophan synthase. DMAPP = ...
  
  Jump to Scheme 6
8. Scheme 7: Iguchi’s total synthesis of clavubicyclone, part 1.
  
  Jump to Scheme 7
9. Scheme 8: Iguchi’s total synthesis of clavubicyclone, part 2.
  
  Jump to Scheme 8
10. Scheme 9: Wender’s syntheses of the two pseudoguainanes confertin (50) and damsinic acid (51) and Pier’s appr...
  
  Jump to Scheme 9
11. Scheme 10: Overman’s total synthesis of scopadulcic acid B.
  
  Jump to Scheme 10
12. Scheme 11: Davies’ total syntheses of tremulenolide A and tremulenediol A.
  
  Jump to Scheme 11
13. Scheme 12: Davies formal [4 + 3] cycloaddition approach towards the formal synthesis of frondosin B.
  
  Jump to Scheme 12
14. Scheme 13: Davies and Sarpongs formal [4 + 3]-cycloaddition approach towards barekoxide (106) and barekol (107...
  
  Jump to Scheme 13
15. Scheme 14: Davies formal [4 + 3]-cycloaddition approach to 5-epi-vibsanin E (115) containing an intermediate c...
  
  Jump to Scheme 14
16. Scheme 15: Echavarren’s total synthesis of schisanwilsonene A (126) featuring an impressive gold-catalzed casc...
  
  Jump to Scheme 15
17. Scheme 16: Davies early example of a formal [4 + 3]-cycloaddition in alkaloids synthesis.
  
  Jump to Scheme 16
18. Scheme 17: Fukuyama’s total synthesis of gelsemine, part 1.
  
  Jump to Scheme 17
19. Scheme 18: Fukuyama’s total synthesis of gelsemine, featuring a divinylcyclopropane rearrangement, part 2.
  
  Jump to Scheme 18
20. Scheme 19: Kende’s total synthesis of isostemofoline, using a formal [4 + 3]-cycloaddition, including an inter...
  
  Jump to Scheme 19
21. Scheme 20: Danishefsky’s total synthesis of gelsemine, part 1.
  
  Jump to Scheme 20
22. Scheme 21: Danishefsky’s total synthesis of gelsemine, part 2.
  
  Jump to Scheme 21
23. Scheme 22: Fukuyama’s total synthesis of gelsemoxonine.
  
  Jump to Scheme 22
24. Scheme 23: Wender’s synthetic access to the core skeleton of tiglianes, daphnanes and ingenanes.
  
  Jump to Scheme 23
25. Scheme 24: Davies’ approach towards the core skeleton of CP-263,114 (212).
  
  Jump to Scheme 24
26. Scheme 25: Wood’s approach towards actinophyllic acid.
  
  Jump to Scheme 25
27. Scheme 26: Takeda’s approach towards the skeleton of the cyanthins, utilitizing the divinylcyclopropane rearra...
  
  Jump to Scheme 26
28. Scheme 27: Donaldson’s organoiron route towards the guianolide skeleton.
  
  Jump to Scheme 27
29. Scheme 28: Stoltz’s tandem Wolff/DVCPR rearrangement.
  
  Jump to Scheme 28
30. Scheme 29: Stephenson’s tandem photocatalysis/arylvinylcyclopropane rearrangement.
  
  Jump to Scheme 29
31. Scheme 30: Padwa’s rhodium cascade involving a DVCPR.
  
  Jump to Scheme 30
32. Scheme 31: Matsubara’s version of a DVCPR.
  
  Jump to Scheme 31
33. Scheme 32: Toste’s tandem gold-catalyzed Claisen-rearrangement/DVCPR.
  
  Jump to Scheme 32
34. Scheme 33: Ruthenium- and gold-catalyzed versions of tandem reactions involving a DVCPR.
  
  Jump to Scheme 33
35. Scheme 34: Tungsten, platinum and gold catalysed cycloisomerizations leading to a DVCPR.
  
  Jump to Scheme 34
36. Scheme 35: Reisman’s total synthesis of salvileucalin B, featuring an (undesired) vinylcyclopropyl carbaldehyd...
  
  Jump to Scheme 35
37. Scheme 36: Studies on the divinylepoxide rearrangement.
  
  Jump to Scheme 36
38. Scheme 37: Studies on the vinylcyclopropanecarbonyl rearrangement.
  
  Jump to Scheme 37
39. Scheme 38: Nitrogen-substituted variants of the divinylcyclopropane rearrangement.
  
  Jump to Scheme 38

Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 163–193, doi:10.3762/bjoc.10.14

Full Text

Synthesis of the B-seco limonoid core scaffold

Hanna Bruss,
Hannah Schuster,
Rémi Martinez,
Markus Kaiser,
Andrey P. Antonchick and
Herbert Waldmann

Full Research Paper
Published 16 Jan 2014

PDF
Album
1. Graphical Abstract
2. Figure 1: Structures of the 4,4,8-trimethyl-17-furanylsteroid core structure I and the representative B-seco ...
  
  Jump to Figure 1
3. Scheme 1: Retrosynthetic analysis of the B-seco limonoid framework employing a [3,3]-sigmatropic rearrangemen...
  
  Jump to Scheme 1
4. Scheme 2: Retrosynthetic analysis of the B-seco limonoid scaffold employing a Claisen rearrangement as key st...
  
  Jump to Scheme 2
5. Scheme 3: Synthesis of alcohols 19, 20 and 22. Reagents and conditions: a) CSA, 2,3-butanedione, trimethyl or...
  
  Jump to Scheme 3
6. Scheme 4: Retrosynthetic analysis of the B-seco limonoid scaffold employing an Ireland–Claisen rearrangement ...
  
  Jump to Scheme 4
7. Scheme 5: Synthesis and Ireland–Claisen rearrangement of the allyl esters 27, 28, 29 and 30. Reagents and con...
  
  Jump to Scheme 5
8. Figure 2: Conformation of rearrangement precursor 30 and possible transition state involved in the Ireland–Cl...
  
  Jump to Figure 2
9. Scheme 6: Synthesis of model C rings 40, 41 and 42. Reagents and conditions: a) TBDPSCl, DMAP, NEt₃, CH₂Cl₂, ...
  
  Jump to Scheme 6
10. Scheme 7: β-Substituted allyl esters tested in the Ireland–Claisen and the Carroll rearrangement.
  
  Jump to Scheme 7
11. Scheme 8: Synthesis and Ireland–Claisen rearrangement of bicyclic allyl ester precursor 66. Reagents and cond...
  
  Jump to Scheme 8
12. Figure 3: Conformations of rearrangement precursors 66 and 77 and possible transition states involved in the ...
  
  Jump to Figure 3
13. Scheme 9: Synthesis and Ireland–Claisen rearrangement of allyl ester 70. Reagents and conditions: a) DIPEA, M...
  
  Jump to Scheme 9
14. Scheme 10: Synthesis and Ireland–Claisen rearrangement of allyl ester 72. Reagents and conditions: a) TIPSOTf,...
  
  Jump to Scheme 10
15. Scheme 11: Synthesis of the C14-epi and C14/C9-epi B-seco limonoid scaffolds 78 and 79. Reagents and condition...
  
  Jump to Scheme 11
16. Scheme 12: Synthesis of fully functionalized A ring 87. Reagents and conditions: a) HO(CH₂)₂OH, THF, Pd/C, H₂,...
  
  Jump to Scheme 12
17. Scheme 13: and Attempted Ireland–Claisen rearrangement of allyl ester 88. R¹ = MOM, R² = CO₂H.
  
  Jump to Scheme 13
18. Scheme 14: Synthesis and attempted Ireland–Claisen rearrangement of allyl ester 93. Reagents and conditions: a...
  
  Jump to Scheme 14
19. Scheme 15: Allyl esters tested in the Ireland–Claisen rearrangement.
  
  Jump to Scheme 15
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 194–208, doi:10.3762/bjoc.10.15

Full Text

Tanzawaic acids I–L: Four new polyketides from Penicillium sp. IBWF104-06

Louis P. Sandjo,
Eckhard Thines,
Till Opatz and
Anja Schüffler

Full Research Paper
Published 22 Jan 2014

PDF
Album
1. Graphical Abstract
2. Figure 1: HMBC, COSY and NOESY correlations of compound 1.
  
  Jump to Figure 1
3. Figure 2: HMBC, COSY and NOESY correlations of compound 2.
  
  Jump to Figure 2
4. Figure 3: HMBC, COSY and NOESY correlations of compound 3.
  
  Jump to Figure 3
5. Figure 4: HMBC, COSY and NOESY correlations of compound 4.
  
  Jump to Figure 4
6. Figure 5: Structures of the isolated compounds.
  
  Jump to Figure 5
7. Figure 6: Crystal structures (ORTEP plot) of arohynapene A (5, left) and tanzawaic acid E (8, right). Thermal...
  
  Jump to Figure 6
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 251–258, doi:10.3762/bjoc.10.20

Full Text

Decandrinin, an unprecedented C₉-spiro-fused 7,8-seco-ent-abietane from the Godavari mangrove Ceriops decandra

Hui Wang,
Min-Yi Li,
Félix Zongwe Katele,
Tirumani Satyanandamurty,
Jun Wu and
Gerhard Bringmann

Full Research Paper
Published 27 Jan 2014

PDF
Album
1. Graphical Abstract
2. Figure 1: Structure of decandrinin (1).
  
  Jump to Figure 1
3. Figure 2: Selected ¹H–¹H COSY and HMBC correlations for decandrinin (1).
  
  Jump to Figure 2
4. Figure 3: Diagnostic NOE interactions for decandrinin (1, B97D/TZVP-optimized structure): arbitrarily the 5R,9...
  
  Jump to Figure 3
5. Figure 4: Determination of the absolute configuration of decandrinin (1) by comparing the calculated CD spect...
  
  Jump to Figure 4
6. Scheme 1: Proposed biosynthetic pathway for decandrinin (1).
  
  Jump to Scheme 1
Supp. Info
Video

Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 276–281, doi:10.3762/bjoc.10.23

Full Text

Total synthesis and cytotoxicity of the marine natural product malevamide D and a photoreactive analog

Werner Telle,
Gerhard Kelter,
Heinz-Herbert Fiebig,
Peter G. Jones and
Thomas Lindel

Full Research Paper
Published 03 Feb 2014

PDF
Album
1. Graphical Abstract
2. Figure 1: Structures of the strongly cytotoxic marine natural products malevamide D (1), isodolastatin H (2),...
  
  Jump to Figure 1
3. Scheme 1: Total synthesis of malevamide D (1). a) DMSO (16 equiv), NEt₃ (5 equiv), pyridine·SO₃ (5 equiv), 0 ...
  
  Jump to Scheme 1
4. Scheme 2: Formation of oxazolylphosphate 18 on attempted DEPC-mediated coupling of dipeptide 15.
  
  Jump to Scheme 2
5. Scheme 3: Synthesis of tosyloximes (Z)-22 and (E)-22, X-ray structure of (E)-22. a) NH₂OH·HCl (1.5 equiv), py...
  
  Jump to Scheme 3
6. Scheme 4: Synthesis of photo malevamide D 30. a) NH₃(l), t-BuOMe, −40 °C, 2 h, rt, 16 h, quant. b) I₂ (1.2 eq...
  
  Jump to Scheme 4
7. Figure 2: DSC curve of diazirine 25, heating rate 5 °C/min.
  
  Jump to Figure 2
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 316–322, doi:10.3762/bjoc.10.29

Full Text

Intermediates in monensin biosynthesis: A late step in biosynthesis of the polyether ionophore monensin is crucial for the integrity of cation binding

Wolfgang Hüttel,
Jonathan B. Spencer and
Peter F. Leadlay

Letter
Published 10 Feb 2014

PDF
Album
1. Graphical Abstract
2. Scheme 1: The proposed pathway for monensin biosynthesis in Streptomyces cinnamonensis. The polyketide syntha...
  
  Jump to Scheme 1
3. Figure 1: LC–MS-analysis of purified monensin-related metabolites. Monensin B derivatives (peaks marked with ...
  
  Jump to Figure 1
4. Figure 2: (a) Crystal structure of sodium demethylmonensin A (4) (ellipsoid probability = 50%); (b) overlay o...
  
  Jump to Figure 2

Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 361–368, doi:10.3762/bjoc.10.34

Full Text

Concise, stereodivergent and highly stereoselective synthesis of cis- and trans-2-substituted 3-hydroxypiperidines – development of a phosphite-driven cyclodehydration

Peter H. Huy,
Julia C. Westphal and
Ari M. P. Koskinen

Full Research Paper
Published 11 Feb 2014

PDF
Album
1. Graphical Abstract
2. Figure 1: Natural products and other bioactive piperidine derivatives of type B.
  
  Jump to Figure 1
3. Figure 2: Retrosynthetic analysis of piperidines B (X = OH or leaving group, PG = protecting group).
  
  Jump to Figure 2
4. Scheme 1: Synthesis of the protected amino acids 2. (a) KOH for 1b. b) PG–X = Cbz–Cl (1a–c), Boc₂O (1d).
  
  Jump to Scheme 1
5. Scheme 2: Synthesis of hydroxy ketones 7 (R = Me (a), Bn (b), Ph (c) and EtSMe (d); PG = Cbz (a–c), Boc (d)).
  
  Jump to Scheme 2
6. Scheme 3: Synthesis of amides 5e and 5f and ketone 7e.
  
  Jump to Scheme 3
7. Scheme 4: Synthesis of amino alcohols syn-9a–d and oxazolidinone 10a. (for 7a–c conditions A: H₂ (1 atm), Pd/...
  
  Jump to Scheme 4
8. Scheme 5: Competition between the Michaelis–Arbuzow process and the desired cyclodehydration of amino alcohol...
  
  Jump to Scheme 5
9. Scheme 6: Initial synthesis of the trans-piperidinol 11a in diminished enantiopurity. ^aThe amino alcohol 9a o...
  
  Jump to Scheme 6
10. Scheme 7: Synthesis of trans-piperidinol 11a in excellent ee.
  
  Jump to Scheme 7
11. Scheme 8: Synthesis of L-733,060·HCl.
  
  Jump to Scheme 8
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 369–383, doi:10.3762/bjoc.10.35

Full Text

Preparation of new alkyne-modified ansamitocins by mutasynthesis

Kirsten Harmrolfs,
Lena Mancuso,
Binia Drung,
Florenz Sasse and
Andreas Kirschning

Full Research Paper
Published 03 Mar 2014

PDF
Album
1. Graphical Abstract
2. Scheme 1: Short representation of ansamitocin biosynthesis.
  
  Jump to Scheme 1
3. Scheme 2: Structures of bromo-ansamitocin derivative 6, folate-ansamitocin P-3 conjugate 7 and thiol 8.
  
  Jump to Scheme 2
4. Scheme 3: Strategies for introducing linker-based thiol groups to the aromatic moiety of ansamitocin P-3 for ...
  
  Jump to Scheme 3
5. Figure 1: m-Aminobenzoic acid derivatives 9–20 tested as mutasynthons.
  
  Jump to Figure 1
6. Scheme 4: Mutasynthetic transformation of aminobenzoic acid 11 with AHBA(−)-mutant of A. pretiosum; putative ...
  
  Jump to Scheme 4
7. Scheme 5: Mutasynthetic transformation of aminobenzoic acid 9 with AHBA(−)-mutant of A. pretiosum to bromo-an...
  
  Jump to Scheme 5
8. Scheme 6: Mutasynthetic transformation of aminobenzoic acids 12 and 13 with AHBA(−)-mutant of A. pretiosum.
  
  Jump to Scheme 6
9. Scheme 7: Mutasynthetic transformation of vinyl(amino)benzoic acid 15 with AHBA(−)-mutant of A. pretiosum.
  
  Jump to Scheme 7
10. Scheme 8: Preparation of thiofunctionalized ansamitocin derivatives 27 by Huisgen-type copper-mediated cycloa...
  
  Jump to Scheme 8
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 535–543, doi:10.3762/bjoc.10.49

Full Text

New sesquiterpene hydroquinones from the Caribbean sponge Aka coralliphagum

Qun Göthel and
Matthias Köck

Full Research Paper
Published 06 Mar 2014

PDF
Album
1. Graphical Abstract
2. Figure 1: Structures of the new compounds siphonodictyals E1–E4 (1–4) and cyclosiphonodictyol A (5) isolated ...
  
  Jump to Figure 1
3. Figure 2: Structures of the related known compounds siphonodictyal B1 (6), siphonodictyal B2 (7), siphonodict...
  
  Jump to Figure 2
4. Figure 3: Selected ¹H,¹³C-HMBC correlations (H → C) and ¹H,¹H-COSY correlation (bold line) observed for sipho...
  
  Jump to Figure 3
5. Figure 4: Selected ¹H,¹³C-HMBC correlations (H → C) observed for siphonodictyal E2 (2).
  
  Jump to Figure 4
6. Figure 5: Possible constitutions for the aromatic moieties of siphonodictyals E2 (2) and E3 (3) (sum over all...
  
  Jump to Figure 5
7. Figure 6: Selected ¹H,¹³C-HMBC correlations (H → C) observed for siphonodictyal E4 (4a).
  
  Jump to Figure 6
8. Figure 7: Proposed biogenesis of 4a starting from the hypothetical precursor 3-ox with an acyclic sesquiterpe...
  
  Jump to Figure 7
9. Figure 8: Hypothetical biogenesis of the bicyclic sesquiterpenoid moiety from the acyclic precursor of the si...
  
  Jump to Figure 8
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 613–621, doi:10.3762/bjoc.10.52

Full Text

Synthesis of complex intermediates for the study of a dehydratase from borrelidin biosynthesis

Frank Hahn,
Nadine Kandziora,
Steffen Friedrich and
Peter F. Leadlay

Full Research Paper
Published 11 Mar 2014

PDF
Album
1. Graphical Abstract
2. Figure 1: a) Structure of borrelidin (1); b) PKS intermediates are attached to an acyl carrier protein domain...
  
  Jump to Figure 1
3. Scheme 1: Retrosynthetic analysis of surrogate substrates for BorDH3 and reference molecules for enzyme assay...
  
  Jump to Scheme 1
4. Scheme 2: Synthesis of the common precursor aldehyde 11. Compound 13 was prepared in six steps and with an ov...
  
  Jump to Scheme 2
5. Scheme 3: Synthesis of the BorDH3 substrates. a) Thiophenolpropionate, Cy₂BCl, Me₂EtN, Et₂O, −78 °C to −20 °C...
  
  Jump to Scheme 3
6. Scheme 4: Synthesis of reference compounds for the BorDH3 assay. a) 24, CH₂Cl₂, 50 °C, 3 h (88% over two step...
  
  Jump to Scheme 4
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 634–640, doi:10.3762/bjoc.10.55

Full Text

Synthesis of (2S,3R)-3-amino-2-hydroxydecanoic acid and its enantiomer: a non-proteinogenic amino acid segment of the linear pentapeptide microginin

Rajendra S. Rohokale and
Dilip D. Dhavale

Full Research Paper
Published 17 Mar 2014

PDF
Album
1. Graphical Abstract
2. Figure 1: Microginin (1) and (2S,3R)-AHDA (2a).
  
  Jump to Figure 1
3. Scheme 1: Retrosynthetic analysis of AHDA.
  
  Jump to Scheme 1
4. Scheme 2: Synthesis of AHDA 2a.
  
  Jump to Scheme 2
5. Scheme 3: Synthesis of ent-AHDA 2b.
  
  Jump to Scheme 3
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 667–671, doi:10.3762/bjoc.10.59

Full Text

Asymmetric total synthesis of a putative sex pheromone component from the parasitoid wasp Trichogramma turkestanica

Danny Geerdink,
Jeffrey Buter,
Teris A. van Beek and
Adriaan J. Minnaard

Full Research Paper
Published 02 Apr 2014

PDF
Album
1. Graphical Abstract
2. Figure 1: Originally proposed structures A and B and revised structures 1 and 2 of putative sex pheromone com...
  
  Jump to Figure 1
3. Scheme 1: Application of the iterative conjugate addition protocol for the preparation of 8.
  
  Jump to Scheme 1
4. Scheme 2: Deoxygenation and desilylation of 8.
  
  Jump to Scheme 2
5. Scheme 3: Vinylogous Horner–Wadsworth–Emmons olefination.
  
  Jump to Scheme 3
6. Scheme 4: Synthesis of α,β-unsaturated ester 15 using a Wittig reaction.
  
  Jump to Scheme 4
7. Scheme 5: Completion of the synthesis of the putative sex pheromone 2.
  
  Jump to Scheme 5
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 761–766, doi:10.3762/bjoc.10.71

Full Text

Structure elucidation of female-specific volatiles released by the parasitoid wasp Trichogramma turkestanica (Hymenoptera: Trichogrammatidae)

Armin Tröger,
Teris A. van Beek,
Martinus E. Huigens,
Isabel M. M. S. Silva,
Maarten A. Posthumus and
Wittko Francke

Full Research Paper
Published 02 Apr 2014

PDF
Album
1. Graphical Abstract
2. Figure 1: Published 70 eV EI mass spectra of the naturally occurring compounds A and B [12].
  
  Jump to Figure 1
3. Figure 2: Synthesis of tetramethyltrideca-2,4-dienes 8, 14 and 15. Conditions: a: LiAlH₄, Et₂O, −30 °C to rt,...
  
  Jump to Figure 2
4. Figure 3: 70 eV EIMS of synthetic tetramethyltrideca-2,4-dienes 8, 14 and 15. These spectra were run under th...
  
  Jump to Figure 3
5. Figure 4: Synthesis of (2E,4EZ)-syn,syn-4,6,8,10-tetramethyltrideca-2,4-diene (22), as well as (2E,4E)- and (2...
  
  Jump to Figure 4
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 767–773, doi:10.3762/bjoc.10.72

Full Text

Amino acid motifs in natural products: synthesis of O-acylated derivatives of (2S,3S)-3-hydroxyleucine

Oliver Ries,
Martin Büschleb,
Markus Granitzka,
Dietmar Stalke and
Christian Ducho

Full Research Paper
Published 16 May 2014

PDF
Album
1. Graphical Abstract
2. Figure 1: Structures of muraymycins A1, B6, C1 and D1 1a–d.
  
  Jump to Figure 1
3. Scheme 1: Synthesis of stereoisomerically pure amino alcohol 5 [32] and of derivative 6 suitable for X-ray crysta...
  
  Jump to Scheme 1
4. Figure 2: Molecular structure of levulinyl ester 6. Anisotropic displacement parameters are depicted at the 5...
  
  Jump to Figure 2
5. Scheme 2: Synthesis of (2S,3S)-3-hydroxyleucine building blocks 13a,b useful for N-derivatization and of the ...
  
  Jump to Scheme 2
6. Scheme 3: Synthesis of (2S,3S)-3-hydroxyleucine building block 19 useful for C-derivatization and of aldehyde ...
  
  Jump to Scheme 3
7. Scheme 4: Synthesis of O-acylated (2S,3S)-3-hydroxyleucine derivatives 27 and 28.
  
  Jump to Scheme 4
8. Scheme 5: Synthesis of 6-methylheptanoic acid (26).
  
  Jump to Scheme 5
9. Scheme 6: Synthesis of Fmoc-protected building blocks 38 and 41 suitable for SPPS, with late-stage side chain...
  
  Jump to Scheme 6
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 1135–1142, doi:10.3762/bjoc.10.113

Full Text

Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery

Jens Schmidt,
Zeinab Khalil,
Robert J. Capon and
Christian B. W. Stark

Letter
Published 26 May 2014

PDF
Album
1. Graphical Abstract
2. Figure 1: Known heronapyrroles A–C and nitropyrrolins A–E.
  
  Jump to Figure 1
3. Scheme 1: Plausible biosynthesis of heronapyrroles A–D.
  
  Jump to Scheme 1
4. Scheme 2: Synthesis of heronapyrrole D.
  
  Jump to Scheme 2
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 1228–1232, doi:10.3762/bjoc.10.121

Full Text

Selective allylic hydroxylation of acyclic terpenoids by CYP154E1 from Thermobifida fusca YX

Anna M. Bogazkaya,
Clemens J. von Bühler,
Sebastian Kriening,
Alexandrine Busch,
Alexander Seifert,
Jürgen Pleiss,
Sabine Laschat and
Vlada B. Urlacher

Full Research Paper
Published 13 Jun 2014

PDF
Album
1. Graphical Abstract
2. Figure 1: Immediate heme surroundings shown for the nearest relative of CYP154E1 with available crystal struc...
  
  Jump to Figure 1
3. Scheme 1: Terpene substrates (grey background) and their oxidised derivatives.
  
  Jump to Scheme 1
4. Scheme 2: a) Ac₂O, pyridine, room temperature, 24 h; b) SeO₂, t-BuOOH, CH₂Cl₂, 0 °C, 5 h; c) K₂CO₃, MeOH, roo...
  
  Jump to Scheme 2
5. Scheme 3: a) SeO₂, t-BuOOH, CH₂Cl₂, 0 °C, 3.5 h.
  
  Jump to Scheme 3
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 1347–1353, doi:10.3762/bjoc.10.137

Full Text

Streptopyridines, volatile pyridine alkaloids produced by Streptomyces sp. FORM5

Ulrike Groenhagen,
Michael Maczka,
Jeroen S. Dickschat and
Stefan Schulz

Full Research Paper
Published 24 Jun 2014

PDF
Album
1. Graphical Abstract
2. Figure 1: Alkaloids produced by Streptomyces strain FORM5.
  
  Jump to Figure 1
3. Figure 2: Part of the total ion chromatogram of the headspace extract of Streptomyces sp. FORM5 with the stru...
  
  Jump to Figure 2
4. Figure 3: Mass spectra of a) (E)-2-(pent-3-en-1-yl)pyridine (streptopyridine E, 8), b) (1Z,3E)-penta-1,3-dien...
  
  Jump to Figure 3
5. Scheme 1: Synthesis of streptopyridines A to E (8–12) and the 2-alkylpyridines 6 and 7.
  
  Jump to Scheme 1
6. Figure 4: Total ion chromatograms of the product mixtures of isomers 9–12 synthesized under E-selective (a) a...
  
  Jump to Figure 4
7. Figure 5: Structures of piperidine derivatives 20–26.
  
  Jump to Figure 5
8. Figure 6: a) Mass spectrum of streptopyridine A (12), b) mass spectrum of 12 after feeding of 2 mM ¹³C₂-sodiu...
  
  Jump to Figure 6
9. Scheme 2: Proposed biosynthesis of the streptopyridines. PKS: polyketide synthase; red: reduction; ta: transa...
  
  Jump to Scheme 2
10. Figure 7: Compounds detected in the headspace of Streptomyces sp. FORM5.
  
  Jump to Figure 7
Supp. Info
Video

Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 1421–1432, doi:10.3762/bjoc.10.146

Full Text

C–H-Functionalization logic guides the synthesis of a carbacyclopamine analog

Sebastian Rabe,
Johann Moschner,
Marina Bantzi,
Philipp Heretsch and
Athanassios Giannis

Full Research Paper
Published 09 Jul 2014

PDF
Album
1. Graphical Abstract
2. Figure 1: Structures of cyclopamine (1) and carbacyclopamine analog 2.
  
  Jump to Figure 1
3. Scheme 1: Retrosynthetic analysis of carbacyclopamine analog 2.
  
  Jump to Scheme 1
4. Scheme 2: Synthesis of carbacyclopamine analog 2.
  
  Jump to Scheme 2
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 1564–1569, doi:10.3762/bjoc.10.161

Full Text

Synthesis and bioactivity of analogues of the marine antibiotic tropodithietic acid

Patrick Rabe,
Tim A. Klapschinski,
Nelson L. Brock,
Christian A. Citron,
Paul D’Alvise,
Lone Gram and
Jeroen S. Dickschat

Letter
Published 06 Aug 2014

PDF
Album
1. Graphical Abstract
2. Figure 1: TDA and related natural products from Phaeobacter inhibens.
  
  Jump to Figure 1
3. Scheme 1: Synthesis of tropone-2-carboxylic acid (13).
  
  Jump to Scheme 1
4. Scheme 2: Synthesis of halogenated TDA analogues.
  
  Jump to Scheme 2
5. Scheme 3: Further compounds included in this SAR study.
  
  Jump to Scheme 3
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 1796–1801, doi:10.3762/bjoc.10.188

Full Text

Sacrolide A, a new antimicrobial and cytotoxic oxylipin macrolide from the edible cyanobacterium Aphanothece sacrum

Naoya Oku,
Miyako Matsumoto,
Kohsuke Yonejima,
Keijiroh Tansei and
Yasuhiro Igarashi

Full Research Paper
Published 07 Aug 2014

PDF
Album
1. Graphical Abstract
2. Figure 1: Structure of sacrolide A (1).
  
  Jump to Figure 1
3. Figure 2: Selected COSY (bold lines) and HMBC (arrows) correlations for sacrolide A (1).
  
  Jump to Figure 2
4. Scheme 1: Initial derivatization strategy for the stereochemical analysis of sacrolide A (1).
  
  Jump to Scheme 1
5. Scheme 2: Determination of the stereochemistry of sacrolide A (1).
  
  Jump to Scheme 2
6. Scheme 3: Plausible biosynthesis of sacrolide A (1).
  
  Jump to Scheme 3
7. Figure 3: The effect of sacrolide A (1) on 3Y1 rat fibroblastic cells. (a) Control. (b) 45 min after exposure...
  
  Jump to Figure 3
8. Figure 4: Extracted ion chromatograms for sacrolide A (1) molecular ion at m/z 307 [M – H]⁻ in the LC–MS anal...
  
  Jump to Figure 4
Supp. Info

Graphical Abstract

Beilstein J. Org. Chem. 2014, 10, 1808–1816, doi:10.3762/bjoc.10.190

Full Text

Back to all Issues

Other Beilstein-Institut Open Science Activities

Keep Informed

RSS Feed

Subscribe to our Latest Articles RSS Feed.

Subscribe

Email Notification

Register and get informed about new articles.

Register

Follow the Beilstein-Institut

Twitter: @BeilsteinInst