First synthesis and determination of the absolute stereochemistry of iso-cladospolide-B and cladospolides-B and C

Sharma, G. V. M.; Reddy, K. Laxma; Reddy, J. Janardhan

doi:10.1016/j.tetlet.2006.07.044

Cited by 26 publications

(9 citation statements)

References 10 publications

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“…43 It is worth noting that other approaches to this class of natural products have used olefin-metathesis, 44 Evans aldol reaction, 45 and Os-catalyzed dihydroxylation 46 transforms. (−)-Phoracantholide J ( 89 ) was previously constructed through either ring-closing metathesis or Ru-catalyzed hydroalkynylation.…”

Section: Methodsmentioning

confidence: 99%

“…Advanced intermediates 82 and 86 have been previously prepared en route to 3–4 and 83 using a Wittig strategy from tartrates that proceeded in 14 steps with 1:5 Z/E olefin selectivity. 43 It is worth noting that other approaches to this class of natural products have used olefin-metathesis, 44 Evans aldol reaction, 45 and Os-catalyzed dihydroxylation 46 transforms. (−)-Phoracantholide J ( 89 ) was previously constructed through either ring-closing metathesis or Ru-catalyzed hydroalkynylation.…”

Section: Methodsmentioning

confidence: 99%

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Decarboxylative alkenylation

Edwards

Merchant

McClymont

et al. 2017

Nature

311

209

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Olefin chemistry, through pericyclic reactions, polymerizations, oxidations, or reductions, plays an essential role in the foundation of how organic matter is manipulated.1 Despite its importance, olefin synthesis still largely relies upon chemistry invented more than three decades ago, with metathesis2 being the most recent addition. Here we describe a simple method to access olefins with any substitution pattern or geometry from one of the most ubiquitous and variegated building blocks of chemistry: alkyl carboxylic acids. The same activating principles used in amide-bond synthesis can thus be employed, under Ni- or Fe-based catalysis, to extract CO2 from a carboxylic acid and economically replace it with an organozinc-derived olefin on mole scale. Over sixty olefins across a range of substrate classes are prepared, and the ability to simplify retrosynthetic analysis is exemplified with the preparation of sixteen different natural products across a range of ten different families.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Decarboxylative alkenylation

Edwards

Merchant

McClymont

et al. 2017

Nature

311

209

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“…We proposed that cyclization of the precursor acid to form berkeley-γ-lactone N ( 8 ) rather than the 16-membered macrolide would proceed with retention of configuration to yield the 4 R 5 S epimer as shown (Figure ). Synthetic studies of the 12-membered macrolide cladospolides and their γ-lactone analogue iso-cladospolide also cyclized with retention of configuration …”

Section: Resultsmentioning

confidence: 99%

“…Synthetic studies of the 12-membered macrolide cladospolides and their γlactone analogue iso-cladospolide also cyclized with retention of configuration. 17 Berkeley-γ-lactone O (9) had a molecular formula of C 20 H 34 O 7 , with 4 degrees of unsaturation, and the additional C 4 H 4 O 3 and NMR spectral data suggestive of a succinate moiety. IR data supported the presence of a γ-lactone (1776 cm −1 ) and a succinate moiety.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Berkeleylactones and a Citreohybriddione Analogue from Penicillium turbatum

Stierle

Alverson

et al. 2021

J. Nat. Prod.

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In 2017 we reported the isolation and characterization of berkeleylactones A−H and A26771B from a coculture of two extremophilic Penicillium sp. isolated from an acid mine waste lake. Berkeleylactone A exhibited potent activity against several strains of multi-drug-resistant Staphylococcus aureus and Bacillus anthracis. A26771B, which is related to the berkeleylactones, also exhibited antibiotic activity. Although the berkeleylactones were novel compounds, A26771B was originally isolated by scientists at Eli Lilly Company from P. turbatum and reported in1977. We recently obtained P. turbatum and grew it in axenic culture. We isolated five new berkeleylactones (2 and 4−7), two berkeley-γ-lactones (8 and 9), and citreohybriddional (10), as well as the known compounds A26771B (1), berkeleylactone E (3), and gliovictin. The structures of the novel compounds were deduced from analysis of spectral data. Compounds 2 and 4 −7 are 16-membered macrolides, while 8 and 9 are γ-lactones that share the hexadecanoic acid skeleton. A26771B (1) and berkeleylactone I (2) were active against several strains of Staphylococcus aureus, including four multi-drug-resistant strains. Berkeleylactone N (8) was active only against Streptococcus pyogenes.

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“…Similarly, CladB and CladC have also received significant attention from synthetic chemists, both being the subject of several synthetic quests (Table ). The first reports of syntheses of CladB were in 2005 .…”

Section: Other Examples Of 12‐membered Macrolactonesmentioning

confidence: 99%

Twelve‐membered macrolactones: privileged scaffolds for the development of new therapeutics

Brzozowski

Wuest

2017

Chem Biol Drug Des

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Natural products commonly produced as secondary metabolites of various plants and micro-organisms represent a diverse chemical space of compounds. The diversity of natural products makes them an attractive target for interrogation by both chemists and biologists alike. Indeed, the study of 12-membered macrolactones has already led to the discovery of lead drug compounds and new biological targets, which has motivated the development of diverted total synthetic routes to libraries of analogs. This review explores the discovery, biological characterization, and synthesis of several 12-membered macrolactones, exploiting examples that underscore their importance in the drug discovery field. It is our hope that this review will motivate further interest in this class of natural products, a group of molecules that we think merit the classification of 'privileged scaffolds' within the medicinal chemistry community, to further investigate and develop novel compounds with promising bioactivity. K E Y W O R D Santibiotic, biosynthesis, diverted total synthesis, macrolactone, natural product

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First synthesis and determination of the absolute stereochemistry of iso-cladospolide-B and cladospolides-B and C

Cited by 26 publications

References 10 publications

Decarboxylative alkenylation

Decarboxylative alkenylation

Berkeleylactones and a Citreohybriddione Analogue from Penicillium turbatum

Twelve‐membered macrolactones: privileged scaffolds for the development of new therapeutics

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