Ireland-Claisen rearrangement of steroidal Δ23-22-alcohols:: an application to Δ22,25-24-alkyl steroid synthesis

被引：11

作者：

Khripach, VA ^{[1
]}

Zhabinskii, VN ^{[1
]}

Konstantinova, OV ^{[1
]}

Khripach, NB ^{[1
]}

机构：

[1] Natl Acad Sci, Inst Bioorgan Chem, Minsk 220141, BELARUS

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 30期

关键词：

Ireland-Claisen rearrangement; steroids and sterols; silicon and compounds; Peterson olefination; 1,4-dienes;

D O I：

10.1016/S0040-4039(00)00900-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for the preparation of a 1,4-diene system in the steroid side chain, providing the possibility of stereocontrol at C-3 has been described. Its usefulness has been examined for Delta(22,25)-24-alkyl steroid synthesis. The proposed approach is based on the Ireland-Claisen rearrangement of Delta(23)-22-alcohols followed by C-25 silylation of the formed ester and Peterson olefination as the final step. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：5765 / 5767

页数：3

共 24 条

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