Chiral base route to cyclic polyols: asymmetric synthesis of aminodeoxyconduritols and conduritol F

被引：16

作者：

de Sousa, SE ^{[1
]}

O'Brien, P ^{[1
]}

Pilgram, CD ^{[1
]}

机构：

[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 45期

基金：

英国工程与自然科学研究理事会;

关键词：

allylic alcohols; cyclitols; epoxides; rearrangement;

D O I：

10.1016/S0040-4039(01)01706-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chiral base route from a meso cyclohexene oxide to an allylic alcohol provides key intermediates for the synthesis of cyclic polyols. A Mitsunobu approach and an Overman rearrangement approach transform allylic alcohols into some aminodeoxyconduritols (95% ee). Elaboration of a chiral enone (89% ee) via (i) alpha -hydroxylation and (ii) stereoselective reduction completes a high yielding synthesis of the tetraacetate of conduritol F. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：8081 / 8083

页数：3

共 32 条

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