埃坡霉素B和D的全合成。
Total syntheses of epothilones B and d.
作者信息
Jung Jae-Chul, Kache Rajashaker, Vines Kimberly K, Zheng Yan-Song, Bijoy Panicker, Valluri Muralikrishna, Avery Mitchell A
机构信息
Department of Medicinal Chemistry, School of Pharmacy, University of Mississippi, P.O. Box 1848, Mississippi 38677-1848, USA.
出版信息
J Org Chem. 2004 Dec 24;69(26):9269-84. doi: 10.1021/jo048742o.
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.
描述了埃坡霉素B（2）和D（4）的汇聚式全合成。关键步骤包括通过诺曼特偶联在C12 - C13处建立所需的（Z）-立体化学、甲基酮28与膦酸酯8的沃兹沃思-埃蒙斯烯化反应、醛5与酮酸衍生物烯醇盐的非对映选择性羟醛缩合以形成C6 - C7键、酸52的选择性脱保护以及大环内酯化反应。
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