Defining the hydrophobic interactions that drive competence stimulating peptide (CSP)-ComD binding in Streptococcus pneumoniae

Bimal Koirala,
Robert A. Hillman,
Erin K. Tiwold,
Michael A. Bertucci and
Yftah Tal-Gan

Full Research Paper
Published 16 Jul 2018

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1. Graphical Abstract
2. Figure 1: The competence regulon QS circuitry in S. pneumoniae. ComC is processed and secreted by ComAB as th...
  
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3. Figure 2: Assessment of protein–peptide binding pockets. Key side-chain residues (black) can either fully occ...
  
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4. Figure 3: Design of CSP1 analogs. The CSP1 sequence is presented using the one-letter amino acid code. Residu...
  
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5. Figure 4: Helical wheel representation of CSP1. The CSP1 residues are presented using the one-letter amino ac...
  
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Beilstein J. Org. Chem. 2018, 14, 1769–1777, doi:10.3762/bjoc.14.151

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Synthesis and photophysical studies of a multivalent photoreactive Ru^II-calix[4]arene complex bearing RGD-containing cyclopentapeptides

Sofia Kajouj,
Lionel Marcelis,
Alice Mattiuzzi,
Adrien Grassin,
Damien Dufour,
Pierre Van Antwerpen,
Didier Boturyn,
Eric Defrancq,
Mathieu Surin,
Julien De Winter,
Pascal Gerbaux,
Ivan Jabin and
Cécile Moucheron

Full Research Paper
Published 16 Jul 2018

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1. Graphical Abstract
2. Figure 1: Targeted multivalent phototherapeutic agent and its calix[4]arene-based precursor. RGD = Arg–Gly–As...
  
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3. Scheme 1: Synthesis of Ru^II-calix[4]arene complex 7.
  
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4. Scheme 2: Synthesis of Ru^II-calix[4]arene-[c-(RGDfK)]₄ conjugate 9.
  
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5. Figure 2: MD snapshot showing an optimized model of conjugate 9. RGDfK units are depicted in orange ribbons, ...
  
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6. Figure 3: Absorption and emission spectra of Ru^II-calix[4]arene-[c-(RGDfK)]₄ conjugate 9 in water.
  
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7. Figure 4: Luminescence intensity and excited state lifetime of conjugate 9 in the presence of GMP measured in...
  
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8. Figure 5: Transient absorption spectra of Ru^II-calix[4]arene-[c-(RGDfK)]₄ conjugate 9 (in 10 mM Tris·HCl buff...
  
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9. Figure 6: MALDI–MS analysis of a solution containing conjugate 9 and GMP after continuous light irradiation. ...
  
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Beilstein J. Org. Chem. 2018, 14, 1758–1768, doi:10.3762/bjoc.14.150

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An amine protecting group deprotectable under nearly neutral oxidative conditions

Shahien Shahsavari,
Chase McNamara,
Mark Sylvester,
Emily Bromley,
Savannah Joslin,
Bao-Yuan Lu and
Shiyue Fang

Full Research Paper
Published 13 Jul 2018

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1. Graphical Abstract
2. Scheme 1: Dmoc and dM-Dmoc protection and deprotection of amines.
  
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3. Scheme 2: Selective deprotection of dM-Dmoc-, Boc- and Fmoc-protected amines.
  
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Beilstein J. Org. Chem. 2018, 14, 1750–1757, doi:10.3762/bjoc.14.149

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DFT calculations on the mechanism of copper-catalysed tandem arylation–cyclisation reactions of alkynes and diaryliodonium salts

Tamás Károly Stenczel,
Ádám Sinai,
Zoltán Novák and
András Stirling

Full Research Paper
Published 12 Jul 2018

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1. Graphical Abstract
2. Scheme 1: Possible intermediates of the interaction of alkynyl compounds with Ar–Cu(III) species.
  
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3. Scheme 2: Two possible reaction routes for the oxazoline formation explored by computations. The schemes indi...
  
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4. Scheme 3: Free energy profiles for the possible reaction routes. The final energy state (−50.5 kcal/mol) is n...
  
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Beilstein J. Org. Chem. 2018, 14, 1743–1749, doi:10.3762/bjoc.14.148

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Synthesis of pyrimido[1,6-a]quinoxalines via intermolecular trapping of thermally generated acyl(quinoxalin-2-yl)ketenes by Schiff bases

Svetlana O. Kasatkina,
Ekaterina E. Stepanova,
Maksim V. Dmitriev,
Ivan G. Mokrushin and
Andrey N. Maslivets

Full Research Paper
Published 11 Jul 2018

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1. Graphical Abstract
2. Figure 1: Quinoxaline-based 6/6/6-angularly fused scaffolds and respective examples of biologically active co...
  
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3. Figure 2: Synthetic routes towards the pyrimido[1,6-a]quinoxaline scaffold.
  
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4. Figure 3: Acyl(quinoxalin-2-yl)ketene.
  
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5. Scheme 1: Thermolysis of five-membered 2,3-dioxoheterocycles resulting in acyl(quinoxalin-2-yl)ketenes.
  
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6. Figure 4: STA plot of thermolysis of PQT 1a. Blue solid curve: DSC; green solid curve: TG; greed dashed curve...
  
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7. Scheme 2: Side-reactions concurring with intermolecular trapping of ketene generated from PQT 1a by benzalani...
  
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8. Figure 5: Scope of the intermolecular trapping of ketenes generated from PQTs 1a–h by Schiff bases 2a–d under...
  
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9. Scheme 3: Formation of furoquinoxalines 6a,b via intramolecular cyclization in ketenes generated from PQTs 1g,...
  
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10. Figure 6: ORTEP drawing of compound 3g (CCDC 1834011) showing thermal ellipsoids at the 30% probability level....
  
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11. Figure 7: ORTEP drawing of compound 3j (CCDC 1834012) showing thermal ellipsoids at the 30% probability level....
  
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Beilstein J. Org. Chem. 2018, 14, 1734–1742, doi:10.3762/bjoc.14.147

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Host–guest complexes of conformationally flexible C-hexyl-2-bromoresorcinarene and aromatic N-oxides: solid-state, solution and computational studies

Rakesh Puttreddy,
Ngong Kodiah Beyeh,
S. Maryamdokht Taimoory,
Daniel Meister,
John F. Trant and
Kari Rissanen

Full Research Paper
Published 10 Jul 2018

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1. Graphical Abstract
2. Figure 1: The chemical structures of C-ethyl-2-bromoresorcinarene (BrC2), C-propyl-2-bromoresorcinarene (BrC3...
  
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3. Figure 2: X-ray crystal structures of (a) 3@BrC6, (b) 4@BrC6, (c) 5@BrC6, (d) 6@BrC6, (e) 7@BrC6, (f) 8@BrC6,...
  
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4. Figure 3: Comparison of X-ray crystal structures (a) 3@BrC2, (c) 3@BrC3, and (e) 3@BrC6 and their DFT-based o...
  
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5. Figure 4: (a) The negative potential localised on the N-oxide oxygen in 3@BrC6 and, (b) the positive charge d...
  
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6. Figure 5: An expansion of the ¹H NMR (6.6 mM at 298 K, 500 MHz) of BrC6 complexes with 3. Spectra are produce...
  
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Beilstein J. Org. Chem. 2018, 14, 1723–1733, doi:10.3762/bjoc.14.146

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Design, synthesis and structure of novel G-2 melamine-based dendrimers incorporating 4-(n-octyloxy)aniline as a peripheral unit

Cristina Morar,
Pedro Lameiras,
Attila Bende,
Gabriel Katona,
Emese Gál and
Mircea Darabantu

Full Research Paper
Published 09 Jul 2018

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1. Graphical Abstract
2. Figure 1: The key elements for design and construction of the targeted G-2 dendrimers.
  
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3. Scheme 1: Convergent versus divergent three steps (a–c) synthesis of central building blocks C1 and C3.
  
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4. Scheme 2: Synthesis of G-1 dendrons D-Cl and D-N<P>NH. *As partial conversions of 1 into 2a and 2b based on t...
  
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5. Scheme 3: Synthesis of G-2 dendrimers 4–6 by m-trimerisations of G-1 dendrons D-Cl and D-N<P>NH.
  
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6. Scheme 4: Synthesis of G-2 dendrimers 7–9 by m-trimerisations of G-1 dendron D-N<P>NH.
  
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7. Figure 2: The three terms rotamerism of G-0 dendrons 2a and 3 about the C(s-triazine)–N(exocyclic) partial do...
  
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8. Figure 3: Comparative details from ¹H NMR spectra of G-2 dendrimer 5 (500 MHz, 5.0 mM in DMSO-d₆).
  
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9. Figure 4: Comparative IR spectra (KBr) of compounds 7a vs 7b (a), 7b vs trimesic acid (b), 8 vs C1 (c) and 9 ...
  
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10. Figure 5: 2D-¹H-DOSY NMR charts (DMSO-d₆, 500 MHz, 298 K) of compounds 7a, 7b (2.5 mM), 8 and 9 (5.0 mM).
  
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11. Figure 6: The DFT optimised geometry at M062X/def2-TZVP level of theory of G-2 dendrimer 7a in DMSO (hydrogen...
  
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12. Figure 7: The DFT optimised geometry at M062X/def2-TZVP level of theory of trimesic tris-carboxylate anion (a...
  
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13. Figure 8: The DFT optimised geometry at M062X/def2-TZVP level of theory of G-2 dendrimers 8 and 9 in DMSO.
  
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14. Figure 9: TEM images of homogeneously packed spherical nano-aggregates (a) and their agglomerations (b) in th...
  
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15. Figure 10: TEM images of homogeneously packed spherical nano-aggregates (a) and their agglomerations (b) in th...
  
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16. Figure 11: Proposed π-stacking interactions in compounds D-N<P>NH and 5–7a.
  
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Beilstein J. Org. Chem. 2018, 14, 1704–1722, doi:10.3762/bjoc.14.145

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Natural and redesigned wasp venom peptides with selective antitumoral activity

Marcelo D. T. Torres,
Gislaine P. Andrade,
Roseli H. Sato,
Cibele N. Pedron,
Tania M. Manieri,
Giselle Cerchiaro,
Anderson O. Ribeiro,
Cesar de la Fuente-Nunez and
Vani X. Oliveira Jr.

Full Research Paper
Published 06 Jul 2018

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1. Graphical Abstract
2. Figure 1: Helical wheel projections of Dec-NH₂ and its analogs, where the yellow circles refer to the hydroph...
  
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3. Figure 2: MTT assays using Dec-NH₂ and its synthetic analogs after 2 and 24 h of exposure to MCF-7 cancer cel...
  
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4. Figure 3: MTT assays evaluating the toxicity of Dec-NH₂ and its derivatives towards MCF-10A normal cells afte...
  
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5. Figure 4: Cell death analysis using flow cytometry. Dot plot graphs from left to right, show cells treated wi...
  
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6. Figure 5: Topological images of untreated MCF-7 cells (A) and cells treated for 24 h with 50 μmol L⁻¹ of Dec-...
  
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Beilstein J. Org. Chem. 2018, 14, 1693–1703, doi:10.3762/bjoc.14.144

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β-Hydroxy sulfides and their syntheses

Mokgethwa B. Marakalala,
Edwin M. Mmutlane and
Henok H. Kinfe

Review
Published 05 Jul 2018

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1. Graphical Abstract
2. Figure 1: Some sulfur-containing natural products.
  
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3. Figure 2: Some natural products incorporating β-hydroxy sulfide moieties.
  
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4. Figure 3: Some synthetic β-hydroxy sulfides of clinical value.
  
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5. Scheme 1: Alumina-mediated synthesis of β-hydroxy sulfides, ethers, amines and selenides from epoxides.
  
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6. Scheme 2: β-Hydroxy sulfide syntheses by ring opening of epoxides under different Lewis and Brønsted acid and...
  
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7. Scheme 3: n-Bu₃P-catalyzed thiolysis of epoxides and aziridines to provide the corresponding β-hydroxy and β-...
  
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8. Scheme 4: Zinc(II) chloride-mediated thiolysis of epoxides.
  
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9. Scheme 5: Thiolysis of epoxides and one-pot oxidation to β-hydroxy sulfoxides under microwave irradiation.
  
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10. Scheme 6: Gallium triflate-catalyzed ring opening of epoxides and one-pot oxidation.
  
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11. Scheme 7: Thiolysis of epoxides and one-pot oxidation to β-hydroxy sulfoxides using Ga(OTf)₃ as a catalyst.
  
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12. Scheme 8: Ring opening of epoxide using ionic liquids under solvent-free conditions.
  
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13. Scheme 9: N-Bromosuccinimide-catalyzed ring opening of epoxides.
  
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14. Scheme 10: LiNTf₂-mediated epoxide opening by thiophenol.
  
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15. Scheme 11: Asymmetric ring-opening of cyclohexene oxide with various thiols catalyzed by zinc L-tartrate.
  
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16. Scheme 12: Catalytic asymmetric ring opening of symmetrical epoxides with t-BuSH catalyzed by (R)-GaLB (43) wi...
  
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17. Scheme 13: Asymmetric ring opening of meso-epoxides by p-xylenedithiol catalyzed by a (S,S)-(salen)Cr complex.
  
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18. Scheme 14: Desymmetrization of meso-epoxide with thiophenol derivatives.
  
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19. Scheme 15: Enantioselective ring-opening reaction of meso-epoxides with ArSH catalyzed by a C₂-symmetric chira...
  
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20. Scheme 16: Enantioselective ring-opening reaction of stilbene oxides with ArSH catalyzed by a C₂-symmetric chi...
  
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21. Scheme 17: Asymmetric desymmetrization of meso-epoxides using BINOL-based Brønsted acid catalysts.
  
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22. Scheme 18: Lithium-BINOL-phosphate-catalyzed desymmetrization of meso-epoxides with aromatic thiols.
  
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23. Scheme 19: Ring-opening reactions of cyclohexene oxide with thiols by using CPs 1-Eu and 2-Tb.
  
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24. Scheme 20: CBS-oxazaborolidine-catalyzed borane reduction of β-keto sulfides.
  
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25. Scheme 21: Preparation of β-hydroxy sulfides via connectivity.
  
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26. Scheme 22: Baker’s yeast-catalyzed reduction of sulfenylated β-ketoesters.
  
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27. Scheme 23: Sodium-mediated ring opening of epoxides.
  
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28. Scheme 24: Disulfide bond cleavage-epoxide opening assisted by tetrathiomolybdate.
  
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29. Scheme 25: Proposed reaction mechanism of disulfide bond cleavage-epoxide opening assisted by tetrathiomolybda...
  
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30. Scheme 26: Cyclodextrin-catalyzed difunctionalization of alkenes.
  
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31. Scheme 27: Zinc-catalyzed synthesis of β-hydroxy sulfides from disulfides and alkenes.
  
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32. Scheme 28: tert-Butyl hydroperoxide-catalyzed hydroxysulfurization of alkenes.
  
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33. Scheme 29: Proposed mechanism of the radical hydroxysulfurization.
  
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34. Scheme 30: Rongalite-mediated synthesis of β-hydroxy sulfides from styrenes and disulfides.
  
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35. Scheme 31: Proposed mechanism of Rongalite-mediated synthesis of β-hydroxy sulfides from styrenes and disulfid...
  
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36. Scheme 32: Copper(II)-catalyzed synthesis of β-hydroxy sulfides 15e,f from alkenes and basic disulfides.
  
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37. Scheme 33: CuI-catalyzed acetoxysulfenylation of alkenes.
  
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38. Scheme 34: CuI-catalyzed acetoxysulfenylation reaction mechanism.
  
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39. Scheme 35: One-pot oxidative 1,2-acetoxysulfenylation of Baylis–Hillman products.
  
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40. Scheme 36: Proposed mechanism for the oxidative 1,2-acetoxysulfination of Baylis–Hillman products.
  
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41. Scheme 37: 1,2-Acetoxysulfenylation of alkenes using DIB/KI.
  
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42. Scheme 38: Proposed reaction mechanism of the diacetoxyiodobenzene (DIB) and KI-mediated 1,2-acetoxysulfenylat...
  
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43. Scheme 39: Catalytic asymmetric thiofunctionalization of unactivated alkenes.
  
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44. Scheme 40: Proposed catalytic cycle for asymmetric sulfenofunctionalization.
  
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45. Scheme 41: Synthesis of thiosugars using intramolecular thiol-ene reaction.
  
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46. Scheme 42: Synthesis of leukotriene C-1 by Corey et al.: (a) N-(trifluoroacetyl)glutathione dimethyl ester (3 ...
  
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47. Scheme 43: Synthesis of pteriatoxins with epoxide thiolysis to attain β-hydroxy sulfides. Reagents: (a) (1) K₂...
  
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48. Scheme 44: Synthesis of peptides containing a β-hydroxy sulfide moiety.
  
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49. Scheme 45: Synthesis of diltiazem (12) using biocatalytic resolution of an epoxide followed by thiolysis.
  
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Beilstein J. Org. Chem. 2018, 14, 1668–1692, doi:10.3762/bjoc.14.143

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Synthesis of diamido-bridged bis-pillar[5]arenes and tris-pillar[5]arenes for construction of unique [1]rotaxanes and bis-[1]rotaxanes

Ying Han,
Li-Ming Xu,
Cui-Yun Nie,
Shuo Jiang,
Jing Sun and
Chao-Guo Yan

Full Research Paper
Published 04 Jul 2018

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1. Graphical Abstract
2. Scheme 1: Synthesis of pillar[5]arene mono(oxyalkoxy)benzoic acids 3a–c.
  
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3. Figure 1: single crystal structure of pillar[5]arene 2a.
  
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4. Figure 2: Single crystal structure of pillar[5]arene 2f.
  
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5. Scheme 2: Synthesis of diamido-bridged bis-pillar[5]arenes 5a–d.
  
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6. Figure 3: The 2D NOSEY spectrum of bis-pillar[5]arene 5d.
  
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7. Scheme 3: Synthesis of pillar[5]arene di(oxyalkoxy)benzoic acid 8.
  
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8. Figure 4: Single crystal structure of pillar[5]arene 7.
  
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9. Scheme 4: Synthesis of diamido-bridged tris-pillar[5]arenes 9a–d.
  
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10. Figure 5: The 2D NOSEY spectra of tris-pillar[5]arene 9d.
  
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Beilstein J. Org. Chem. 2018, 14, 1660–1667, doi:10.3762/bjoc.14.142

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Heterogeneous acidic catalysts for the tetrahydropyranylation of alcohols and phenols in green ethereal solvents

Ugo Azzena,
Massimo Carraro,
Gloria Modugno,
Luisa Pisano and
Luigi Urtis

Letter
Published 03 Jul 2018

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1. Graphical Abstract
2. Scheme 1: Synthesis of THP ether 3a.
  
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3. Scheme 2: Synthesis of THP ethers 3b–l in the presence of NH₄HSO₄@SiO₂. All reactions were run at rt, in the ...
  
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4. Scheme 3: Deprotection of THP ether 3i.
  
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5. Scheme 4: One-pot synthesis of 3-[4-(tetrahydro-2H-pyran-2-yl)oxymethylphenyl]-3-pentanol (4fa).
  
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6. Scheme 5: One-pot synthesis of 4-(tetrahydro-2H-pyran-2-yloxymethyl)benzyl alcohol (4fb).
  
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Beilstein J. Org. Chem. 2018, 14, 1655–1659, doi:10.3762/bjoc.14.141

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The phenyl vinyl ether–methanol complex: a model system for quantum chemistry benchmarking

Dominic Bernhard,
Fabian Dietrich,
Mariyam Fatima,
Cristóbal Pérez,
Hannes C. Gottschalk,
Axel Wuttke,
Ricardo A. Mata,
Martin A. Suhm,
Melanie Schnell and
Markus Gerhards

Full Research Paper
Published 02 Jul 2018

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1. Graphical Abstract
2. Figure 1: Minimum structures of the most stable PVE–MeOH dimers obtained at the B3LYP-D3(BJ)/def2-TZVP level;...
  
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3. Figure 2: Dispersion interaction density (DID) plots calculated at the LCCSD/VQZ-F12 level. The brown zones i...
  
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4. Figure 3: FTIR spectra of the supersonic expansion of methanol (MeOH) and phenyl vinyl ether (PVE) at differe...
  
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5. Figure 4: The IR/R2PI spectrum in the range of 3520–3750 cm⁻¹ was obtained via the excitation energy of 36885...
  
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6. Figure 5: A section of the experimental 2–8 GHz spectrum using a mixture of PVE and MeOH (3 million acquisiti...
  
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7. Figure 6: UV/IR/UV spectrum of PVE–MeOH in the range of 3520–3750 cm⁻¹; excitation laser: 36741 cm⁻¹, ionizin...
  
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Beilstein J. Org. Chem. 2018, 14, 1642–1654, doi:10.3762/bjoc.14.140

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Visible light-mediated difluoroalkylation of electron-deficient alkenes

Vyacheslav I. Supranovich,
Vitalij V. Levin,
Marina I. Struchkova,
Jinbo Hu and
Alexander D. Dilman

Letter
Published 02 Jul 2018

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1. Graphical Abstract
2. Scheme 1: Fluoroalkylation of alkenes.
  
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3. Figure 1: Difluoroalkylation of alkenes. Isolated yields are shown. ^a2 equiv of the alkene were used.
  
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4. Scheme 2: Proposed mechanism.
  
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Beilstein J. Org. Chem. 2018, 14, 1637–1641, doi:10.3762/bjoc.14.139

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Anomeric modification of carbohydrates using the Mitsunobu reaction

Julia Hain,
Patrick Rollin,
Werner Klaffke and
Thisbe K. Lindhorst

Review
Published 29 Jun 2018

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1. Graphical Abstract
2. Scheme 1: Left: The Mitsunobu reaction is essentially a nucleophilic substitution of alcohols occurring with ...
  
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3. Scheme 2: Mechanistic considerations on the Mitsunobu reaction with carbohydrate hemiacetals (depicted in sim...
  
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4. Scheme 3: Anomeric esterification using the Mitsunobu procedure [29].
  
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5. Scheme 4: Conversion of allyl glucuronate into various 1-O-esterified allyl glucuronates using anomeric Mitsu...
  
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6. Scheme 5: Synthesis of anomeric glycosyl esters as substrates for Au-catalyzed glycosylation [40].
  
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7. Scheme 6: Correlation between pK_a value of the employed acids (or alcohol) and the favoured anomeric configur...
  
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8. Scheme 7: Synthesis of the β-mannosyl phosphates for the synthesis of HBP 43 by anomeric phosphorylation acco...
  
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9. Scheme 8: Synthesis of phenyl glycosides 44 and 45 from unprotected sugars [24].
  
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10. Scheme 9: Synthesis of azobenzene mannosides 47 and 48 without protecting group chemistry [46].
  
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11. Scheme 10: Synthesis of various aryl sialosides using Mitsunobu glycosylation [25].
  
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12. Scheme 11: Mitsunobu synthesis of different jadomycins [54,55]. BOM: benzyloxymethyl.
  
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13. Scheme 12: Stereoselectivity in the Mitsunobu synthesis of catechol glycosides in the gluco- and manno-series [56]....
  
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14. Scheme 13: Formation of a 1,2-cis glycoside 80 assisted by steric hindrance of the β-face of the disaccharide ...
  
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15. Scheme 14: Stereoselective β-D-mannoside synthesis [60].
  
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16. Scheme 15: TIPS-assisted synthesis of 1,2-cis arabinofuranosides [63]. TIPS: triisopropylsilyl.
  
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17. Scheme 16: The Mitsunobu reaction with glycals leads to interesting rearrangement products [69].
  
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18. Scheme 17: Synthesis of disaccharides using mercury(II) bromide as co-activator in the Mitsunobu reaction [75].
  
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19. Scheme 18: Synthesis of various fructofuranosides according to Mitsunobu and proposed neighbouring group parti...
  
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20. Scheme 19: The Mitsunobu reaction allows stereoslective acetalization of dihydroartemisinin [77].
  
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21. Scheme 20: Synthesis of alkyl thioglycosides by Mitsunobu reaction [81].
  
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22. Scheme 21: Preparation of iminoglycosylphthalimide 115 from 114 [85].
  
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23. Scheme 22: Mitsunobu reaction as a key step in the total synthesis of aurantoside G [87].
  
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24. Scheme 23: Utilization of an N–H acid in the Mitsunobu reaction [88].
  
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25. Scheme 24: Mitsunobu reaction with 1H-tetrazole [89].
  
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26. Scheme 25: Formation of a rebeccamycin analogue using the Mitsunobu reaction [101].
  
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27. Scheme 26: Synthesis of carbohydrates with an alkoxyamine bond [114].
  
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28. Scheme 27: Synthesis of glycosyl fluorides and glycosyl azides according to Mitsunobu [118,119].
  
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29. Scheme 28: Anomeric oxidation under Mitsunobu conditions [122].
  
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Beilstein J. Org. Chem. 2018, 14, 1619–1636, doi:10.3762/bjoc.14.138

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Glycosylation reactions mediated by hypervalent iodine: application to the synthesis of nucleosides and carbohydrates

Yuichi Yoshimura,
Hideaki Wakamatsu,
Yoshihiro Natori,
Yukako Saito and
Noriaki Minakawa

Review
Published 28 Jun 2018

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1. Graphical Abstract
2. Figure 1: Design of potential antineoplastic nucleosides.
  
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3. Scheme 1: Synthesis of 4’-thioDMDC.
  
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4. Scheme 2: Synthesis of 4’-thioribonucleosides by Minakawa and Matsuda.
  
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5. Scheme 3: Synthesis of 4’-thioribonucleosides by Yoshimura.
  
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6. Figure 2: Concept of the Pummerer-type glycosylation and hypervalent iodine-mediated glycosylation.
  
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7. Scheme 4: Oxidative glycosylation of 4-thioribose mediated by hypervalent iodine.
  
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8. Figure 3: Speculated mechanism of oxidative glycosylation mediated by hypervalent iodine.
  
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9. Scheme 5: Synthesis of purine 4’-thioribonucleosides using hypervalent iodine-mediated glycosylation.
  
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10. Scheme 6: Unexpected glycosylation of a thietanose derivative.
  
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11. Scheme 7: Speculated mechanism of the ring expansion of a thietanose derivative.
  
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12. Scheme 8: Synthesis of thietanonucleosides using the Pummerer-type glycosylation.
  
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13. Scheme 9: First synthesis of 4’-selenonucleosides.
  
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14. Scheme 10: The Pummerer-type glycosylation of 4-selenoxide 74.
  
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15. Scheme 11: Synthesis of purine 4’-selenonucleosides using hypervalent iodine-mediated glycosylation.
  
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16. Figure 4: Concept of the oxidative coupling reaction applicable to the synthesis of carbocyclic nucleosides.
  
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17. Scheme 12: Oxidative coupling reaction mediated by hypervalent iodine.
  
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18. Scheme 13: Synthesis of cyclohexenyl nucleosides using an oxidative coupling reaction.
  
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19. Figure 5: Concept of the oxidative coupling reaction of glycal derivatives.
  
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20. Scheme 14: Oxidative coupling reaction of silylated uracil and DHP using hypervalent iodine.
  
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21. Scheme 15: Proposed mechanism of the oxidative coupling reaction mediated by hypervalent iodine.
  
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22. Figure 6: Synthesis of 2’,3’-unsaturated nucleosides using hypervalent iodine and a co-catalyst.
  
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23. Scheme 16: Synthesis of dihydropyranonucleoside.
  
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24. Scheme 17: Synthesis of acetoxyacetals using hypervalent iodine and addition of silylated base.
  
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25. Scheme 18: One-pot fragmentation-nucleophilic additions mediated by hypervalent iodine.
  
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26. Figure 7: The reaction of thioglycoside with hypervalent iodine in the presence of Lewis acids.
  
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27. Scheme 19: Synthesis of disaccharides employing thioglycosides under an oxidative coupling reaction mediated b...
  
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28. Scheme 20: Synthesis of disaccharides using disarmed thioglycosides by hypervalent iodine-mediated glycosylati...
  
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29. Scheme 21: Glycosylation using aryl(trifluoroethyl)iodium triflimide.
  
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30. Figure 8: Expected mechanism of hypervalent iodine-mediated glycosylation with glycals.
  
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31. Scheme 22: Synthesis of oligosaccharides by hypervalent iodine-mediated glycosylation with glycals.
  
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32. Scheme 23: Synthesis of 2-deoxy amino acid glycosides.
  
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33. Figure 9: Rationale for the intramolecular migration of the amino acid unit.
  
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Beilstein J. Org. Chem. 2018, 14, 1595–1618, doi:10.3762/bjoc.14.137

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Drug targeting to decrease cardiotoxicity – determination of the cytotoxic effect of GnRH-based conjugates containing doxorubicin, daunorubicin and methotrexate on human cardiomyocytes and endothelial cells

Livia Polgár,
Eszter Lajkó,
Pál Soós,
Orsolya Láng,
Marilena Manea,
Béla Merkely,
Gábor Mező and
László Kőhidai

Full Research Paper
Published 28 Jun 2018

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1. Graphical Abstract
2. Figure 1: Chemical structures of the GnRH-drug conjugates synthesized and investigated in the present work. A...
  
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3. Figure 2: Chemical structures of the bifunctional GnRH-drug conjugates synthesized and investigated in the pr...
  
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4. Figure 3: Long-term cytotoxic effects – impedimetrically registered negative effect on cell proliferation/via...
  
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5. Figure 4: Long-term cytotoxic effects – impedimetrically registered negative effect on cell proliferation and...
  
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Beilstein J. Org. Chem. 2018, 14, 1583–1594, doi:10.3762/bjoc.14.136

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Direct electrochemical generation of organic carbonates by dehydrogenative coupling

Tile Gieshoff,
Vinh Trieu,
Jan Heijl and
Siegfried R. Waldvogel

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Published 27 Jun 2018

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1. Graphical Abstract
2. Figure 1: Current non-phosgene approaches to organic carbonates.
  
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3. Scheme 1: Preparation of tetrabutylammonium methyl carbonate by direct carbon dioxide incorporation.
  
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4. Scheme 2: Direct generation of mesityl methyl carbonate by dehydrogenative functionalization.
  
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5. Figure 2: Influence of the electrode distance; ^{a 1}H NMR yield; ^bisolated yield.
  
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Beilstein J. Org. Chem. 2018, 14, 1578–1582, doi:10.3762/bjoc.14.135

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A conformationally adaptive macrocycle: conformational complexity and host–guest chemistry of zorb[4]arene

Liu-Pan Yang,
Song-Bo Lu,
Arto Valkonen,
Fangfang Pan,
Kari Rissanen and
Wei Jiang

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Published 27 Jun 2018

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1. Graphical Abstract
2. Scheme 1: (a) Chemical structures of ZB4 and the guests involved in this research. The counterions are PF₆⁻. ...
  
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3. Figure 1: X-ray single crystal structure of ZB4 and the host–guest complexes. a) ZB4, b) 2⁺@ZB4-IV, c) 3⁺@ZB4...
  
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4. Figure 2: Parabolic free-energy relationship between log(K_R/K_H) and Hammett parameter σ_p. K_R: guests 11⁺–21⁺; ...
  
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5. Figure 3: X-ray single crystal structures of 14⁺@ZB4-III, 16⁺@ZB4-III, 18⁺@ZB4-III and 21⁺@ZB4-III. Butyl gro...
  
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6. Figure 4: X-ray single crystal structures of 18⁺@ZB4-III and 18⁺ in 18⁺@ZB4-III.
  
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7. Figure 5: Linear relationships of ΔH with temperature (left, slope = −0.13, R² = 0.9956) and TΔS (right, slop...
  
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Beilstein J. Org. Chem. 2018, 14, 1570–1577, doi:10.3762/bjoc.14.134

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Phosphoramidite building blocks with protected nitroxides for the synthesis of spin-labeled DNA and RNA

Timo Weinrich,
Eva A. Jaumann,
Ute M. Scheffer,
Thomas F. Prisner and
Michael W. Göbel

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Published 26 Jun 2018

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1. Graphical Abstract
2. Figure 1: Structures of TEMPO-labeled oligonucleotides and of phosphoramidites 5–8.
  
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3. Scheme 1: Synthesis of phosphoramidite 5. Reagents and conditions: (a) 1. 2,4,6-triisopropylbenzenesulfonyl c...
  
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4. Scheme 2: Synthesis of phosphoramidite 7. Reagents and conditions: (a) Addition of 10, diisopropylethylamine,...
  
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5. Scheme 3: Synthesis of phosphoramidite 8. Reagents and conditions: (a) Addition of 10, diisopropylethylamine,...
  
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6. Figure 2: Structures of palindromic oligonucleotides prepared from amidites 5 (22a, 23a), 7 (24a, 25a), and 8...
  
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7. Figure 3: PELDOR measurement of 24c (12mer dA). The background-corrected time trace (original time trace in Supporting Information File 1,...
  
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Beilstein J. Org. Chem. 2018, 14, 1563–1569, doi:10.3762/bjoc.14.133

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Lanyamycin, a macrolide antibiotic from Sorangium cellulosum, strain Soce 481 (Myxobacteria)

Lucky S. Mulwa,
Rolf Jansen,
Dimas F. Praditya,
Kathrin I. Mohr,
Patrick W. Okanya,
Joachim Wink,
Eike Steinmann and
Marc Stadler

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Published 26 Jun 2018

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1. Graphical Abstract
2. Figure 1: Lanyamycin (1/2), differing at C-26, isolated from Sorangium cellulosum (Soce 481).
  
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3. Figure 2: Structure fragments of lanyamycin (1/2) from ¹H,¹H-COSY spectrum (bold bonds) and selected ¹H,¹³C-H...
  
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4. Figure 3: Structure of bafilomycin A₁.
  
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5. Figure 4: 3D Model of the macrolactone ring of lanyamycin (1/2) and selected ROESY correlations. Green arrows...
  
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6. Figure 5: HCV assay: NC = negative control, EGCG = positive control, Cpd1 = lanyamycin (1/2).
  
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Beilstein J. Org. Chem. 2018, 14, 1554–1562, doi:10.3762/bjoc.14.132

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Thiocarbonyl-enabled ferrocene C–H nitrogenation by cobalt(III) catalysis: thermal and mechanochemical

Santhivardhana Reddy Yetra,
Zhigao Shen,
Hui Wang and
Lutz Ackermann

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Published 25 Jun 2018

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1. Graphical Abstract
2. Figure 1: Selected ferrocene-based ligands and organocatalysts.
  
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3. Scheme 1: Scope of substituted dioxazolones 2.
  
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4. Scheme 2: C–H Amidation of arylated ferrocenes 1.
  
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5. Scheme 3: Thiocarbonyl-assisted C–H amidation.
  
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6. Scheme 4: H/D Exchange reactions.
  
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7. Scheme 5: Intermolecular competition experiments.
  
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8. Scheme 6: Synthesis of aminoketone 4aa.
  
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9. Scheme 7: Mechanochemical ferrocene C–H nitrogenation.
  
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Beilstein J. Org. Chem. 2018, 14, 1546–1553, doi:10.3762/bjoc.14.131

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Cobalt-catalyzed C–H cyanations: Insights into the reaction mechanism and the role of London dispersion

Eric Detmar,
Valentin Müller,
Daniel Zell,
Lutz Ackermann and
Martin Breugst

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Published 25 Jun 2018

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1. Graphical Abstract
2. Scheme 1: Cycloaddition reaction of in situ generated benzynes resulting in the sterically more hindered addu...
  
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3. Scheme 2: Recently developed cobalt-catalyzed C–H cyanation [30].
  
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4. Figure 1: Calculated free-energy profile for the cobalt-catalyzed C–H cyanation of 2-phenylpyridine (1a) [in ...
  
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5. Figure 2: Calculated structures, selected bond lengths (in Å), and imaginary frequencies for representative i...
  
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6. Scheme 3: Kinetic profile of the cobalt-catalyzed C–H cyanation with differently substituted cyanating agents ...
  
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7. Figure 3: Noncovalent interaction (NCI) analysis for selected intermediates and transition states. The gradie...
  
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8. Figure 4: Projected dispersion interaction density (DID) plots for selected intermediates and transition stat...
  
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Beilstein J. Org. Chem. 2018, 14, 1537–1545, doi:10.3762/bjoc.14.130

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Mild and selective reduction of aldehydes utilising sodium dithionite under flow conditions

Nicole C. Neyt and
Darren L. Riley

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Published 22 Jun 2018

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1. Graphical Abstract
2. Scheme 1: Sodium dithionite-mediated reductions under basic conditions.
  
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3. Figure 1: Uniqsis FlowSyn Stainless Steel Flow reactor.
  
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4. Figure 2: Flow reactor configuration for the reduction of aldehydes and ketones.
  
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5. Figure 3: NMR spectra showing the optimisation of the dithionite reduction for the reduction of benzaldehyde.
  
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6. Figure 4: Selective reduction of an aldehyde in the presence of a ketone.
  
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7. Figure 5: Flow reactor set-up for the continuous reduction of aldehydes.
  
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Beilstein J. Org. Chem. 2018, 14, 1529–1536, doi:10.3762/bjoc.14.129

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Hypervalent organoiodine compounds: from reagents to valuable building blocks in synthesis

Gwendal Grelier,
Benjamin Darses and
Philippe Dauban

Review
Published 21 Jun 2018

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1. Graphical Abstract
2. Scheme 1: Strategies to address the issue of sustainability with polyvalent organoiodine reagents.
  
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3. Scheme 2: Functionalization of ketones and alkenes with IBX.
  
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4. Scheme 3: Functionalization of pyrroles with DMP.
  
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5. Scheme 4: Catalytic benzoyloxy-trifluoromethylation reported by Szabó.
  
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6. Scheme 5: Catalytic benzoyloxy-trifluoromethylation reported by Mideoka.
  
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7. Scheme 6: Catalytic 1,4-benzoyloxy-trifluoromethylation of dienes.
  
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8. Scheme 7: Catalytic benzoyloxy-trifluoromethylation of allylamines.
  
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9. Scheme 8: Catalytic benzoyloxy-trifluoromethylation of enynes.
  
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10. Scheme 9: Catalytic benzoyloxy-trifluoromethylation of allenes.
  
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11. Scheme 10: Alkynylation of N-(aryl)imines with EBX for the formation of furans.
  
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12. Scheme 11: Catalytic benzoyloxy-alkynylation of diazo compounds.
  
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13. Scheme 12: Catalytic asymmetric benzoyloxy-alkynylation of diazo compounds.
  
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14. Scheme 13: Catalytic 1,2-benzoyloxy-azidation of alkenes.
  
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15. Scheme 14: Catalytic 1,2-benzoyloxy-azidation of enamides.
  
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16. Scheme 15: Catalytic 1,2-benzoyloxy-iodination of alkenes.
  
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17. Scheme 16: Seminal study with cyclic diaryl-λ³-iodane.
  
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18. Scheme 17: Synthesis of alkylidenefluorenes from cyclic diaryl-λ³-iodanes.
  
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19. Scheme 18: Synthesis of alkyne-substituted alkylidenefluorenes.
  
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20. Scheme 19: Synthesis of phenanthrenes from cyclic diaryl-λ³-iodanes.
  
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21. Scheme 20: Synthesis of dibenzocarbazoles from cyclic diaryl-λ³-iodanes.
  
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22. Scheme 21: Synthesis of triazolophenantridines from cyclic diaryl-λ³-iodanes.
  
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23. Scheme 22: Synthesis of functionalized benzoxazoles from cyclic diaryl-λ³-iodanes.
  
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24. Scheme 23: Sequential difunctionalization of cyclic diaryl-λ³-iodanes.
  
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25. Scheme 24: Double Suzuki–Miyaura coupling reaction of cyclic diaryl-λ³-iodanes.
  
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26. Scheme 25: Synthesis of a δ-carboline from cyclic diaryl-λ³-iodane.
  
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27. Scheme 26: Synthesis of N-(aryl)carbazoles from cyclic diaryl-λ³-iodanes.
  
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28. Scheme 27: Synthesis of carbazoles from cyclic diaryl-λ³-iodanes.
  
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29. Scheme 28: Synthesis of carbazoles and acridines from cyclic diaryl-λ³-iodanes.
  
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30. Scheme 29: Synthesis of dibenzothiophenes from cyclic diaryl-λ³-iodanes.
  
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31. Scheme 30: Synthesis of various sulfur heterocycles from cyclic diaryl-λ³-iodanes.
  
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32. Scheme 31: Synthesis of dibenzothioheterocycles from cyclic diaryl-λ³-iodanes.
  
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33. Scheme 32: Synthesis of dibenzosulfides and dibenzoselenides from cyclic diaryl-λ³-iodanes.
  
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34. Scheme 33: Synthesis of dibenzosulfones from cyclic diaryl-λ³-iodanes.
  
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35. Scheme 34: Seminal study with linear diaryl-λ³-iodanes.
  
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36. Scheme 35: N-Arylation of benzotriazole with symmetrical diaryl-λ³-iodanes.
  
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37. Scheme 36: Tandem catalytic C–H/N–H arylation of indoles with diaryl-λ³-iodanes.
  
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38. Scheme 37: Tandem N-arylation/C(sp²)–H arylation with diaryl-λ³-iodanes.
  
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39. Scheme 38: Catalytic intermolecular diarylation of anilines with diaryl-λ³-iodanes.
  
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40. Scheme 39: Catalytic synthesis of diarylsulfides with diaryl-λ³-iodanes.
  
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41. Scheme 40: α-Arylation of enolates using [bis(trifluoroacetoxy)iodo]arenes.
  
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42. Scheme 41: Mechanism of the α-arylation using [bis(trifluoroacetoxy)iodo]arene.
  
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43. Scheme 42: Catalytic nitrene additions mediated by [bis(acyloxy)iodo]arenes.
  
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44. Scheme 43: Tandem of C(sp³)–H amination/sila-Sonogashira–Hagihara coupling.
  
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45. Scheme 44: Tandem reaction using a λ³-iodane as an oxidant, a substrate and a coupling partner.
  
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46. Scheme 45: Synthesis of 1,2-diarylated acrylamidines with ArI(OAc)₂.
  
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Beilstein J. Org. Chem. 2018, 14, 1508–1528, doi:10.3762/bjoc.14.128

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Hyper-reticulated calixarene polymers: a new example of entirely synthetic nanosponge materials

Alberto Spinella,
Marco Russo,
Antonella Di Vincenzo,
Delia Chillura Martino and
Paolo Lo Meo

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Published 20 Jun 2018

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1. Graphical Abstract
2. Scheme 1: Structures of: a) calixarene Ca-OP; b) alkyl diazides A1–A4.
  
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3. Scheme 2: Structures of p-nitroaniline derivatives 1–5 and dyes 6–10.
  
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4. Figure 1: FTIR spectra of Ca-OP (red), A2 (green) and CaNS2 (blue).
  
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5. Figure 2: a) ¹³C{¹H} CP-MAS NMR spectra of CaNSs; b) signal attributions.
  
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6. Figure 3: Selection of SEM micrographs for materials for CaNS1 (a), CaNS2 (b), CaNS3 (c) and CaNS4 (d).
  
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