Synthetic studies on bafilomycin A1:: stereoselective synthesis of the enantiopure C1-C11 fragment

被引：17

作者：

Quéron, E ^{[1
]}

Lett, R ^{[1
]}

机构：

[1] CNRS, AVENTIS Pharma, Unite Mixte, UMR 26, F-93235 Romainville, France

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 23期

关键词：

epoxides; aluminium and compounds; alkynes; zirconium; and compounds; silyl ether selective oxidation; Wittig reactions;

D O I：

10.1016/j.tetiet.2004.04.033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the enantiopure C-1-C-11 fragment of bafilomycin A(1) has been achieved with a 4% overall yield over 18 steps from (R)-(+)-citronellol. Key steps involve Sharpless asymmetric epoxidation, Miyashita reaction of a gamma,delta-epoxymethacrylate with trimethylaluminum in the presence of water, bis-OTMS selective Swern oxidations, Corey-Fuchs alkyne formation, Negishi's carbometalation, and stereoselective formation of the C-2-C-3 trisubstituted bond of the conjugated diene by a Wittig-type olefination of the alpha, beta-unsaturated C-3-C-11 aldehyde with the ylide derived from the readily available phosphonium salt [Cl-, Ph3P+CH(OMe)COOMe]. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：4527 / 4531

页数：5

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