Natural products in synthesis and biosynthesis II
Natural products continue to be an inspiring field of research and an important source of potent biologically active compounds. Currently, also in the pharmaceutical industry, natural products are experiencing a revival as viable drug candidates, which is a pleasing development since many infectious diseases continue to threaten human health. From the numerous articles in daily newspapers, it is obvious that politicians have also realised the urgent need for new drugs and the potential associated with natural products and their derivatives. Certainly, the recent technological advances in many fields related to natural products, analytical chemistry, gene synthesis, and genome sequencing and editing offer an efficient toolbox to natural products chemists. In addition, classical methods such as isotopic labelling experiments continue to be important.
See also the Thematic Series:
Natural products in synthesis and biosynthesis
Biosynthesis and function of secondary metabolites
- Review
- Published 09 Dec 2015
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Figure 1: Structures of lovastatin (1), aflatoxin B1 (2) and amphotericin B (3).
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Scheme 1: a) Structure of rhizoxin (4). b) Two possible mechanisms of chain branching catalysed by a branchin...
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Scheme 2: Structure of coelimycin P1 (8) and proposed biosynthetic formation from the putative PKS produced a...
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Scheme 3: Structure of trioxacarcin A (9) with highlighted carbon origins of the polyketide core from acetate...
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Scheme 4: Proposed biosynthetic assembly of clostrubin A (12). Bold bonds show intact acetate units.
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Figure 2: Structure of forazoline A (13).
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Figure 3: Structures of tyrocidine A (14) and teixobactin (15).
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Figure 4: Top: Structure of the NRPS product kollosin A (16) with the sequence N-formyl-D-Leu-L-Ala-D-Leu-L-V...
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Scheme 5: Proposed biosynthesis of aspirochlorine (20) via 18 and 19.
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Scheme 6: Two different macrocyclization mechanisms in the biosynthesis of pyrrocidine A (24).
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Figure 5: Structure of thiomarinol A (27). Bold bonds indicate carbon atoms derived from 4-hydroxybutyrate.
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Figure 6: Structures of artemisinin (28), ingenol (29) and paclitaxel (30).
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Figure 7: The revised (31) and the previously suggested (32) structure of hypodoratoxide and the structure of...
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Figure 8: Structure of the two interconvertible conformers of (1(10)E,4E)-germacradien-6-ol (34) studied with...
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Scheme 7: Proposed cyclization mechanism of corvol ethers A (42) and B (43) with the investigated reprotonati...
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Scheme 8: Predicted (top) and observed (bottom) 13C-labeling pattern in cyclooctatin (45) after feeding of [U-...
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Scheme 9: Proposed mechanism of the cyclooctat-9-en-7-ol (52) biosynthesis catalysed by CotB2. Annotated hydr...
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Scheme 10: Cyclization mechanism of sesterfisherol (59). Bold lines indicate acetate units; black circles repr...
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Scheme 11: Cyclization mechanisms to pentalenene (65) and protoillud-6-ene (67).
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Scheme 12: Reactions of chorismate catalyzed by three different enzyme subfamilies. Oxygen atoms originating f...
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Scheme 13: Incorporation of sulfur into tropodithietic acid (72) via cysteine.
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Scheme 14: Biosynthetic proposal for the starter unit of antimycin biosynthesis. The hydrogens at positions R1...
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- Review
- Published 10 Dec 2015
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Figure 1: a) Structure of xenicin (1) and b) numbering of the xenicane skeleton according to Schmitz and van ...
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Figure 2: Overview of selected Xenia diterpenoids according to the four subclasses [2-20]. The nine-membered carboc...
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Figure 3: Representative members of the caryophyllenes, azamilides and Dictyota diterpenes.
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Scheme 1: Proposed biosynthesis of Xenia diterpenoids (OPP = pyrophosphate, GGPP = geranylgeranyl pyrophospha...
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Scheme 2: Direct synthesis of the nine-membered carbocycle as proposed by Schmitz and van der Helm (E = elect...
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Scheme 3: The construction of E- or Z-cyclononenes.
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Scheme 4: Total synthesis of racemic β-caryophyllene (22) by Corey.
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Scheme 5: Total synthesis of racemic β-caryophyllene (22) by Oishi.
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Scheme 6: Total synthesis of coraxeniolide A (10) by Leumann.
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Scheme 7: Total synthesis of antheliolide A (18) by Corey.
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Scheme 8: a) Synthesis of enantiomer 80, b) total syntheses of coraxeniolide A (10) and c) β-caryophyllene (22...
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Scheme 9: Total synthesis of blumiolide C (11) by Altmann.
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Scheme 10: Synthesis of a xeniolide F precursor by Hiersemann.
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Scheme 11: Synthesis of the xenibellol (15) and the umbellacetal (114) core by Danishefsky.
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Scheme 12: Proposed biosynthesis of plumisclerin A (118).
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Scheme 13: Synthesis of the tricyclic core structure of plumisclerin A by Yao.
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Scheme 14: Total synthesis of 4-hydroxydictyolactone (137) by Williams.
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Scheme 15: Photoisomerization of 4-hydroxydictyolactone (137) to 4-hydroxycrenulide (138).
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Scheme 16: The total synthesis of (+)-acetoxycrenulide (151) by Paquette.
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- Review
- Published 19 Feb 2016
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Figure 1: Flow chart of the typical characterization of chemical signals from microbial interactions. (1) Che...
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Figure 2: Multilateral microbe–insect interactions. (1) Insect–symbiont interactions with both partners benef...
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Figure 3: a) Interactions between bacterial (endo)symbionts and insects with both partners benefiting from th...
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Figure 4: Multilateral microbial interactions in fungus-growing insects. (1) Insect cultivar: protects and sh...
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Figure 5: Small molecules (chemical mediators) play key roles in maintaining garden homeostasis in fungus-gro...
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Figure 6: Secondary metabolites isolated from Actinobacteria from fungus-growing termites. Microtermolide A (...
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Figure 7: Secondary metabolites from bacterial mutualists of solitary insects. Bafilomycin A1 (21), bafilomyc...
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Figure 8: Beneficial interactions (1) between fungal symbionts and insects.
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Figure 9: Secondary metabolites isolated from fungal symbionts. Cerulenin (30), helvolic acid (31), lepiochlo...
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Figure 10: Predatory interactions, (1) entomopathogenic fungi use insect as prey.
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Figure 11: Entomopathogenic fungi use secondary metabolites as insecticidal compounds to kill their prey. Dest...
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- Review
- Published 29 Feb 2016
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Figure 1: Representative terpenes.
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Figure 2: Two different models showing how energy evolves throughout the course of a reaction: (a) a two-dime...
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Figure 3: A depiction of the “snowboarder” analogy for reactions displaying non-statistical dynamic effects. ...
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Figure 4: The tetramethylbromonium ion system [14].
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Figure 5: The reaction mechanisms of interest in the PES and dynamics studies of Dupuis and co-workers (R = CH...
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Figure 6: The portion of the norborn-2-en-7-ylmethyl cation PES examined by Ghigo et al. [60]. Energies reported ...
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Figure 7: The transformation of 2-norbornyl cation to 1,3-dimethylcyclopentyl cation.
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Figure 8: Carbocation rearrangements for which trajectory calculations were used to estimate lifetimes of sec...
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Figure 9: Carbocation rearrangements involved in abietadiene formation.
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Figure 10: Carbocation rearrangements involved in miltiradiene formation.
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Figure 11: Top: carbocation rearrangements involved in epi-isozizaene formation. Bottom: reaction coordinate d...
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Correction
- Review
- Published 24 Mar 2016
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Figure 1: Selected monocyclic and monobenzo α-pyrone structures.
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Figure 2: The basic core structure of dibenzo-α-pyrones.
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Figure 3: Selected dibenzo-α-pyrones.
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Figure 4: Structure of ellagic acid and of the urolithins, the latter metabolized from ellagic acid by intest...
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Figure 5: Structure of murayalactone, the only dibenzo-α-pyrone described from bacteria.
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Figure 6: Structures of the 6-pentyl-2-pyrone (29) and of trichopyrone (30). Only 29 showed antifungal activi...
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Figure 7: Selected monocyclic α-pyrones.
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Figure 8: Structures of the gibepyrones A–F.
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Figure 9: Structures of the phomenins A and B.
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Figure 10: Structures of monocyclic α-pyrones showing pheromone (47) and antitumor activity (48), respectively....
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Figure 11: Structures of 6-alkyl (alkoxy or alkylthio)-4-aryl-3-(4-methanesulfonylphenyl)pyrones.
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Figure 12: Structures of kavalactones.
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Figure 13: Strutures of germicins.
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Figure 14: Structures of the pseudopyronines.
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Figure 15: The structures of the monobenzo-α-pyrone anticoagulant drugs warfarin and phenprocoumon.
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Figure 16: Structures of selected monobenzo-α-pyrones.
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Figure 17: Hypothetical pathway of 29 generation from linoleic acid [34].
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Figure 18: Proposed biosynthetic pathway of alternariol (modified from [77]). Malonyl-CoA building blocks are appl...
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Figure 19: Structures of phenylnannolones and of enterocin, both biosynthesized via polyketide synthase system...
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Figure 20: Pyrone ring formation. Examples for the three types of PKS systems are shown in A–C. In D the mecha...
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Figure 21: Structures of csypyrones.
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Figure 22: Schematic drawing of the T-shaped catalytic cavities of the related enzymes CorB and MxnB. The two ...
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Figure 23: Stereo representation of the CorB binding situation (modified from [89]). The substrate mimic (dark vio...
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Figure 24: Proposed mechanism for the CsyB enzymatic reaction. A) Coupling reaction of the β-keto fatty acyl i...
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Figure 25: Proposed biosynthesis of photopyrone D (37) by the enzyme PpyS from P. luminescens (modified from [63])...
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- Review
- Published 30 Mar 2016
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Figure 1: Natural products isolated from M. xanthus DK1622. DKxanthene-534 (1); myxalamid B (2); myxovirescin...
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Figure 2: Vegetative cells of P. fallax HKI 727 under a phase-contrast microscope (K. Martin, unpublished). B...
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Figure 3: Structures of myxopyronins A (11) and B (12), corallopyronins A (13), B (14) and C (15), as well as...
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Figure 4: Structure of althiomycin (17).
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Figure 5: Structures of cystobactamids 919-1 (18), 919-2 (19), and 507 (20).
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Figure 6: Structures of natural products isolated from Herpetosiphon spp.: siphonazole (21); auriculamide (22...
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- Review
- Published 22 Apr 2016
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Figure 1: Structures of the naturally occurring muraymycins isolated by McDonald et al. [22].
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Figure 2: Structures of selected classes of nucleoside antibiotics. Similarities to the muraymycins are highl...
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Figure 3: Structure of peptidoglycan. Long chains of glycosides (alternating GlcNAc (green) and MurNAc (blue)...
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Figure 4: Schematic representation of bacterial cell wall biosynthesis.
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Figure 5: Translocase I (MraY) catalyses the reaction of UDP-MurNAc-pentapeptide with undecaprenyl phosphate ...
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Figure 6: Proposed mechanisms for the MraY-catalysed reaction. A: Two-step mechanism postulated by Heydanek e...
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Scheme 1: First synthetic access towards simplified muraymycin analogues as reported by Yamashita et al. [76].
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Scheme 2: Synthesis of (+)-caprazol (19) reported by Ichikawa, Matsuda et al. [92].
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Scheme 3: Synthesis of the epicapreomycidine-containing urea dipeptide via C–H activation [96,97].
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Scheme 4: Synthesis of muraymycin D2 and its epimer reported by Ichikawa, Matsuda et al. [96,97].
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Scheme 5: Synthesis of the urea tripeptide unit as a building block for muraymycins reported by Kurosu et al. ...
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Scheme 6: Synthesis of the uridine-derived core structure of naturally occuring muraymycins reported by Ducho...
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Scheme 7: Synthesis of the epicapreomycidine-containing urea dipeptide from Garner's aldehyde reported by Duc...
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Scheme 8: Synthesis of a hydroxyleucine-derived aldehyde building block reported by Ducho et al. [107].
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Scheme 9: Synthesis of 5'-deoxy muraymycin C4 (65) as a closely related natural product analogue [78,109,110].
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Figure 7: Summary of modifications on semisynthetic muraymycin analogues tested by Lin et al. [86]. Most active c...
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Figure 8: Bioactive muraymycin analogues identified by Yamashita et al. [76].
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Figure 9: Muraymycin D2 and several non-natural lipidated analogues 91a–d [77,114].
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Figure 10: Non-natural muraymycin analogues with varying peptide structures [77,114].
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Figure 11: SAR results for several structural variations of the muraymycin scaffold.
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Figure 12: Muraymycin analogues designed for potential anti-Pseudomonas activity (most active analogues are hi...
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Scheme 10: Proposed outline pathway for muraymycin biosynthesis based on the analysis of the biosynthetic gene...
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Scheme 11: Biosynthesis of the nucleoside core structure of A-90289 antibiotics (which is identical to the mur...
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Scheme 12: Transaldolase-catalysed formation of the key intermediate GlyU 101 in the biosynthesis of muraymyci...
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- Review
- Published 13 May 2016
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Figure 1: Structures of cystobactamids 507, 919-1 and 919-2.
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Figure 2: Structures of aurafuron A and corallopyronin A.
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Figure 3: Structures of ixabepilone and capecitabine.
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Figure 4: Structures of DKxanthene-534 and myxochelin A.
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Figure 5: Phylogenetic tree of halotolerant and halophilic myxobacteria. The neighbor-joining tree is based o...
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Figure 6: Structure of nannocystin A.
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Figure 7: Structure of phenylnannolones A–C.
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Figure 8: Structures of the pyrronazols, dihydroxyphenazin and 1-hydroxyphenazin-6-yl-α-D-arabinofuranoside.
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Figure 9: Structures of nannozinones A + B and nannochelin A from N. pusilla strain MNa10913.
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Figure 10: Structure of haliangicin from H. ochraceum.
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Figure 11: Structure of haliamide from H. ochraceum SMP-2.
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Figure 12: Structures of salimabromide, enhygrolides A + B and salimyxins A + B.
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Figure 13: Structures of miuraenamides A–F from P. miuraensis.
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Supp. Info
- Review
- Published 20 Jun 2016
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Figure 1: Schematic of RiPP biosynthesis. Thiazole/oxazole formation is represented by the blue heterocycle (...
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Figure 2: Examples of heterocycles in RiPPs alongside the precursor peptides that these molecules derive from...
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Figure 3: Formation of thiazoles and oxazoles in RiPPs. A) Biosynthesis of microcin B17. B) Mechanistic model...
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Figure 4: Lanthionine bond formation. A) Nisin and its precursor peptide. B) Mechanism of lanthionine bond fo...
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Figure 5: S-[(Z)-2-Aminovinyl]-D-cysteine (AviCys) formation in the epidermin pathway. A) Mechanisms for deca...
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Figure 6: Cyclisation in the biosynthesis of thiopeptides. A) Mechanism of TclM-catalysed heterocyclisation i...
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Figure 7: ATP-dependent macrocyclisation. A) General mechanism for ATP-dependent macrolactonisation or macrol...
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Figure 8: Peptidase-like macrolactam formation. A) General mechanism. B) Examples of RiPPs cyclised by serine...
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Figure 9: Structure of autoinducing peptide AIP-I from Staphylococcus aureus and the sequence of the correspo...
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Figure 10: Radical cyclisation in RiPP biosynthesis. A) AlbA-catalysed formation of thioethers in the biosynth...
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Figure 11: RiPPs with uncharacterised mechanisms of cyclisation. Unusual heterocycles in ComX and methanobacti...
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- Review
- Published 20 Jul 2016
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Scheme 1: Schematic description of the cyclisation reaction catalysed by TE domains. In most cases, the nucle...
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Scheme 2: Mechanisms for the formation of oxygen heterocycles. The degree of substitution can differ from tha...
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Scheme 3: Pyran-ring formation in pederin (24) biosynthesis. Incubation of recombinant PedPS7 with substrate ...
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Scheme 4: The domain AmbDH3 from ambruticin biosynthesis catalyses the dehydration of 25 and subsequent cycli...
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Scheme 5: SalBIII catalyses dehydration of 29 and subsequent cyclisation to tetrahydropyran 30 [18].
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Figure 1: All pyranonaphtoquinones contain either the naphtha[2,3-c]pyran-5,10-dione (32) or the regioisomeri...
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Scheme 6: Pyran-ring formation in actinorhodin (34) biosynthesis. DNPA: 4-dihydro-9-hydroxy-1-methyl-10-oxo-3H...
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Scheme 7: Pyran formation in granaticin (36) biosynthesis. DNPA: 4-dihydro-9-hydroxy-1-methyl-10-oxo-3H-napht...
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Scheme 8: Pyran formation in alnumycin (37) biosynthesis. Adapted from [21].
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Scheme 9: Biosynthesis of pseudomonic acid A (61). The pyran ring is initially formed in 57 after dehydrogena...
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Scheme 10: Epoxidation–cyclisation leads to the formation of the tetrahydropyran ring in the western part of t...
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Scheme 11: a) Nonactin (70) is formed from heterodimers of (−)(+)-dimeric nonactic acid and (+)(−)-dimeric non...
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Figure 2: Pamamycins (73) are macrodiolide antibiotics containing three tetrahydrofuran moieties, which are a...
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Scheme 12: A PS domain homolog in oocydin A (76) biosynthesis is proposed to catalyse furan formation via an o...
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Scheme 13: Mechanism of oxidation–furan cyclisation by AurH, which converts (+)-deoxyaureothin (77) into (+)-a...
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Scheme 14: Leupyrrin A2 (80) and the proposed biosynthesis of its furylidene moiety [69,70].
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Scheme 15: Asperfuranone (93) biosynthesis, adapted from [75].
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Figure 3: The four major aflatoxins produced by Aspergilli are the types B1, B2, G1 and G2 (94–97). In the di...
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Scheme 16: Overview on aflatoxin B1 (94) biosynthesis. HOMST = 11-hydroxy-O-methylsterigmatocystin [78,79,82-106].
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Scheme 17: A zipper mechanism leads to the formation of oxygen heterocycles in monensin biosynthesis [109-111].
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Scheme 18: Formation of the 2,6-dioxabicyclo[3.2.1]octane (DBO) ring system in aurovertin B (118) biosynthesis ...
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Figure 4: Structures of the epoxide-containing polyketides epothilone A (119) and oleandomycin (120) [123-125].
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Scheme 19: Structures of phoslactomycin B (121) (a) and jerangolid A (122) (b). The heterocycle-forming steps ...
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Scheme 20: a) Structures of rhizoxin (130) and cycloheximide (131). Model for the formation of δ-lactones (b) ...
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Scheme 21: EncM catalyses a dual oxidation sequence and following processing of the highly reactive intermedia...
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Figure 5: Mesomeric structures of tetronates [138,139].
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Figure 6: Structures of tetronates for which gene clusters have been sequenced. The tetronate moiety is shown...
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Scheme 22: Conserved steps for formation and processing in several 3-acyl-tetronate biosynthetic pathways were...
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Scheme 23: In versipelostatin A (153) biosynthesis, VstJ is a candidate enzyme for catalysing the [4 + 2] cycl...
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Scheme 24: a) Structures of some thiotetronate antibiotics. b) Biosynthesis of thiolactomycin (165) as propose...
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Scheme 25: Aureusidine synthase (AS) catalyses phenolic oxidation and conjugate addition of chalcones leading ...
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Scheme 26: a) Oxidative cyclisation is a key step in the biosynthesis of spirobenzofuranes 189, 192 and 193. b...
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Scheme 27: A bicyclisation mechanism forms a β-lactone and a pyrrolidinone and removes the precursor from the ...
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Scheme 28: Spontaneous cyclisation leads to off-loading of ebelactone A (201) from the PKS machinery [163].
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Scheme 29: Mechanisms for the formation of nitrogen heterocycles.
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Scheme 30: Biosynthesis of highly substituted α-pyridinones. a) Feeding experiments confirmed the polyketide o...
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Scheme 31: Acridone synthase (ACS) catalyses the formation of 1,3-dihydroxy-N-methylacridone (224) by condensa...
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Scheme 32: A Dieckmann condensation leads to the formation of a 3-acyl-4-hydroxypyridin-2-one 227 and removes ...
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Scheme 33: a) Biosynthesis of the pyridinone tenellin (234). b) A radical mechanism was proposed for the ring-...
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Scheme 34: a) Oxazole-containing PKS–NRPS-derived natural products oxazolomycin (244) and conglobatin (245). b...
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Scheme 35: Structure of tetramic acids 251 (a) and major tautomers of 3-acyltetramic acids 252a–d (b). Adapted...
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Scheme 36: Equisetin biosynthesis. R*: terminal reductive domain. Adapted from [202].
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Scheme 37: a) Polyketides for which a similar biosynthetic logic was suggested. b) Pseurotin A (256) biosynthe...
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Figure 7: Representative examples of PTMs with varying ring sizes and oxidation patterns [205,206].
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Scheme 38: Ikarugamycin biosynthesis. Adapted from [209-211].
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Scheme 39: Tetramate formation in pyrroindomycin aglycone (279) biosynthesis [213-215].
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Scheme 40: Dieckmann cyclases catalyse tetramate or 2-pyridone formation in the biosynthesis of, for example, ...
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- Review
- Published 30 Sep 2016
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Scheme 1: Putative structures of geraniol 1a (R = H) or 1b (R = H) (in 1924), their expected dihydroxylation ...
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Scheme 2: Correlation between the substrate double bond geometry and relative stereochemistry of the correspo...
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Scheme 3: Mechanisms and classification for the metal-mediated oxidative cyclizations to form 2,5-disubstitut...
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Scheme 4: Synthesis of (+)-anhydro-D-glucitol and (+)-D-chitaric acid using an OsO4-mediated oxidative cycliz...
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Scheme 5: Total synthesis of neodysiherbaine A via a Ru(VIII)- and an Os(VI)-catalyzed oxidative cyclization,...
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Scheme 6: Formal synthesis of ionomycin by Kocienski and co-workers.
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Scheme 7: Total synthesis of amphidinolide F by Fürstner and co-workers.
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Scheme 8: Brown`s and Donohoe`s oxidative cyclization approach to cis-solamin A.
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Scheme 9: Total synthesis of cis-solamin A using a Ru(VIII)-catalyzed oxidative cyclization and enzymatic des...
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Scheme 10: Donohoe´s double oxidative cyclization approach to cis-sylvaticin.
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Scheme 11: Permanganate-mediated approach to cis-sylvaticin by Brown and co-workers.
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Scheme 12: Total synthesis of membranacin using a KMnO4-mediated oxidative cyclization.
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Scheme 13: Total synthesis of membrarollin and its analogue 21,22-diepi-membrarollin.
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Scheme 14: Total synthesis of rollidecin C and D using a late stage Re(VII)-catalyzed oxidative polycyclizatio...
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Scheme 15: Co(II)-catalyzed oxidative cyclization in the total synthesis of asimilobin and gigantetrocin A.
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Scheme 16: Mn(VII)-catalyzed oxidative cyclization of a 1,5-diene in the synthesis of trans-(+)-linalool oxide....
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Scheme 17: Re(VII)-catalyzed oxidative cyclization in the total synthesis of teurilene.
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Scheme 18: Total synthesis of (+)-eurylene via Re(VII)- and Cr(VI)-mediated oxidative cyclizations.
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Scheme 19: Synthesis of cis- and trans-THF Rings of eurylene via Mn(VII)-mediated oxidative cyclizations.
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Scheme 20: Cr(VI)-catalyzed oxidative cyclization in the total synthesis of venustatriol by Corey et al.
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Scheme 21: Ru(VIII)-catalyzed oxidative cyclization of a 1,5-diene in the synthesis and evaluation of its ster...
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Scheme 22: Ru(VII)-catalyzed oxidative cyclization of a 5,6-dihydroxy alkene in the synthesis of the core stru...
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- Review
- Published 07 Nov 2016
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Figure 1: Structures of the enduracididine family of amino acids (1–6).
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Figure 2: Enduracidin A (7) and B (8).
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Figure 3: Minosaminomycin (9) and related antibiotic kasugamycin (10).
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Figure 4: Enduracididine-containing compound 11 identified in a cytotoxic extract of Leptoclinides dubius [32].
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Figure 5: Mannopeptimycins α–ε (12–16).
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Figure 6: Regions of the mannopeptimycin structure investigated in structure–activity relationship investigat...
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Figure 7: Teixobactin (17).
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Scheme 1: Proposed biosynthesis of L-enduracididine (1) and L-β-hydroxyenduracididine (5).
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Scheme 2: Synthesis of enduracididine (1) by Shiba et al.
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Scheme 3: Synthesis of protected enduracididine diastereomers 31 and 32.
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Scheme 4: Synthesis of the C-2 azido diastereomers 36 and 37.
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Scheme 5: Synthesis of 2-azido-β-hydroxyenduracididine derivatives 38 and 39.
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Scheme 6: Synthesis of protected β-hydroxyenduracididine derivatives 40 and 41.
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Scheme 7: Synthesis of C-2 diastereomeric amino acids 46 and 47.
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Scheme 8: Synthesis of protected β-hydroxyenduracididines 51 and 52.
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Scheme 9: General transformation of alkenes to cyclic sulfonamide 54 via aziridine intermediate 53.
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Scheme 10: Synthesis of (±)-enduracididine (1) and (±)-allo-enduracididine (3).
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Scheme 11: Synthesis of L-allo-enduracididine (3).
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Scheme 12: Synthesis of protected L-allo-enduracididine 63.
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Scheme 13: Synthesis of β-hydroxyenduracididine derivative 69.
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Scheme 14: Synthesis of minosaminomycin (9).
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Scheme 15: Retrosynthetic analysis of mannopeptimycin aglycone (77).
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Scheme 16: Synthesis of protected amino acids 87 and 88.
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Scheme 17: Synthesis of mannopeptimycin aglycone (77).
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Scheme 18: Synthesis of N-mannosylation model guanidine 92 and attempted synthesis of benzyl protected mannosy...
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Scheme 19: Synthesis of benzyl protected mannosyl D-β-hydroxyenduracididine 97.
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Scheme 20: Synthesis of L-β-hydroxyenduracididine 98.
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Scheme 21: Total synthesis of mannopeptimycin α (12) and β (13).
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Scheme 22: Synthesis of protected L-allo-enduracididine 102.
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Scheme 23: The solid phase synthesis of teixobactin (17).
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Scheme 24: Retrosynthesis of the macrocyclic core 109 of teixobactin (17).
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Scheme 25: Synthesis of macrocycle 117.
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