An efficient total synthesis of isodrimeninol from zamoranic acid

被引：0

作者：

Marcos, IS ^{[1
]}

Moro, RF ^{[1
]}

Carballares, S ^{[1
]}

Urones, JG ^{[1
]}

机构：

[1] Univ Salamanca, Dept Quim Organ, E-37008 Salamanca, Spain

来源：

SYNLETT | 2000年 / 04期

关键词：

regioselective acid-catalysed elimination; gamma-lactones; delta-lactones; bioactive drimanes; diastereoselective epoxidation;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient total synthesis of isodrimeninol (1) has been achieved from zamoranic acid (3) employing a regioselective Lewis acid mediated elimination-isomerisation as the key step. Following oxidative cleavage of the resulting conjugated diene to the methyl ketone, standard manipulations allowed the synthesis of allylic alcohols 10 which, after a highly diastereoselective epoxidation and subsequent lactonisation, allowed the synthesis of the natural product in 11 steps and 56% overall yield.

引用

页码：541 / 543

页数：3

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