Total synthesis of (+)-brefeldin A

被引：34

作者：

Wu, Yikang ^{[1
]}

Gao, Jian ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 08期

关键词：

D O I：

10.1021/ol800137f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+)-Brefeldin A was synthesized through an efficient route, which features (1) construction of the five-membered ring from a Crimmins aldol via tandem Li-I exchange and carbanion-mediated cyclization with concurrent removal of the chiral auxiliary, (2) introduction of the lower side chain (C10 to C16) via a Rh-catalyzed Michael addition of a vinyl boronic acid, (3) stereoselective reduction of the C7 ketone with SmI(2), and (4) a 2-methyl-6-nitrobenzoic anhydride-mediated (Shiina) lactonization.

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页码：1533 / 1536

页数：4

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