Stereoselective approach to alk-2-yne-1,4-diols. Application to the synthesis of musclide B

被引：30

作者：

Amador, M ^{[1
]}

Ariza, X ^{[1
]}

Garcia, J ^{[1
]}

Ortiz, J ^{[1
]}

机构：

[1] Univ Barcelona, Dept Quim Organ, Barcelona 08028, Spain

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 15期

关键词：

D O I：

10.1016/S0040-4039(02)00395-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An expedient method for the stereoselective preparation of alk-2-yne-1,4-diols has been achieved. based on the addition of chiral alk-1-yn-3-ols (or their protected derivatives) to aldehydes mediated by zinc triflate. Et3N, and (+)- or (-)-N-methylephedrine. In general. the configuration observed at the emergent stereocenter depends on the N-methylephedrine employed resulting in good to excellent diastereoselectivities. This strategy has been applied to the enantioselective synthesis of musclide B. a bioactive metabolite front musk. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：2691 / 2694

页数：4

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