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Total syntheses of epothilones B and D

Authors :
Jae-Chul Jung
Kache, Rajashaker
Vines, Kimberly K.
Yan-Song Zheng
Bijoy, Panicker
Valluri, Muralikrishna
Avery, Mitchell A.
Source :
Journal of Organic Chemistry. Dec 24, 2004, Vol. 69 Issue 26, p9269, 16 p.
Publication Year :
2004

Abstract

A convergent, total synthesis of epothilones B and D is described. The key steps are Normant coupling to establish the desired (Z)-stereochemistry at C12-C13, Wadsworth-Emmons olefination of methyl ketone with the phosphonate ester, diastereoselective aldol condensation of aldehyde with the enolate of keto acid derivatives to form the C6-C7 bond, selective deprotection of acid 52, and macrolactonization.

Details

Language :
English
ISSN :
00223263
Volume :
69
Issue :
26
Database :
Gale General OneFile
Journal :
Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
edsgcl.127675596