Total Synthesis of (+)-Brefeldin C, (+)-nor-Me Brefeldin A and (+)-4-epi-nor-Me Brefeldin A

被引：21

作者：

Archambaud, Sylvie ^{[1
]}

Legrand, Frederic ^{[1
]}

Aphecetche-Julienne, Karine ^{[1
]}

Collet, Sylvain ^{[1
]}

Guingant, Andre ^{[1
]}

Evain, M. ^{[2
]}

机构：

[1] Univ Nantes, CNRS, UMR 6230, F-44322 Nantes 3, France

[2] Inst Mat Jean Rouxel, F-44322 Nantes 03, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 07期

关键词：

G protein; Brefeldin A analogues; Desymmetrization; Macrolactonization; Macrocycles; Asymmetric synthesis; Total synthesis; MACROLIDE ANTIBIOTICS; ASYMMETRIC-SYNTHESIS; GUANINE-NUCLEOTIDE; ENANTIOSELECTIVE SYNTHESIS; CYCLIC ANHYDRIDES; DIRECT ADDITION; BIOSYNTHESIS; EXCHANGE; ALDEHYDES; DECUMBIN;

D O I：

10.1002/ejoc.200901233

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total synthesis of (+)-brefeldin C (BFC) and two brefeldin A (BFA) analogues - (+)-nor-Me BFA and (+)-4-epi-nor-Me BFA - has been developed, Key features of the syntheses include desymmetrization of meso anhydrides, a Carreira reaction to control the absolute configuration at C4 of BFC, a Suzuki-Miyaura cross-coupling reaction to create the C11-C12 bond and a Yamaguchi reaction to form the 13-membered lactone ring.

引用

页码：1364 / 1380

页数：17

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