AN EFFICIENT ENANTIOSELECTIVE SYNTHESIS OF (-)-SERRICOROLE

被引：31

作者：

OPPOLZER, W

RODRIGUEZ, I

机构：

[1] Département de Chimie Organique, Université de Genève, Genève

来源：

HELVETICA CHIMICA ACTA | 1993年 / 76卷 / 03期

关键词：

D O I：

10.1002/hlca.19930760314

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The cigarette beetle pheromone (-)-serricorole (1) has been synthesized in 23 % overall yield by an eight-step sequence starting from N-propionylsultam 3. The synthesis features asymmetric anti- and syn- aldolizations 3 --> 4 and 8 --> 9, a non-destructive N-acylsultam cleavage with lithiated ethylphenylsulfone (10 --> 12), and the smooth, Ti-mediated cyclization of beta-acyloxy-ketone 2 to dihydropyranone 14.

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页码：1275 / 1281

页数：7

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