Total Syntheses of Epothilones B and D

A convergent, total synthesis of epothilones B (2) and D (4) is described. The key steps are Normant coupling to establish the desired (Z)-stereochemistry at C12−C13, Wadsworth−Emmons olefination of methyl ketone 28 with the phosphonate ester 8, diastereoselective aldol condensation of aldehyde 5 wi...

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Bibliographic Details
Published in:Journal of organic chemistry 2004-12, Vol.69 (26), p.9269-9284
Main Authors: Jung, Jae-Chul, Kache, Rajashaker, Vines, Kimberly K, Zheng, Yan-Song, Bijoy, Panicker, Valluri, Muralikrishna, Avery, Mitchell A
Format: Article
Language:English
Subjects:
Chemistry
Epothilones - chemical synthesis
Epothilones - chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Magnetic Resonance Spectroscopy
Mass Spectrometry
Molecular Structure
Organic chemistry
Preparations and properties
Spectrophotometry, Infrared
Stereoisomerism
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Summary:A convergent, total synthesis of epothilones B (2) and D (4) is described. The key steps are Normant coupling to establish the desired (Z)-stereochemistry at C12−C13, Wadsworth−Emmons olefination of methyl ketone 28 with the phosphonate ester 8, diastereoselective aldol condensation of aldehyde 5 with the enolate of keto acid derivatives to form the C6−C7 bond, selective deprotection of acid 52, and macrolactonization.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo048742o