An efficient enantioselective synthesis of (+)-disparlure

被引：22

作者：

Hu, SJ ^{[1
]}

Jayaraman, S ^{[1
]}

Oehlschlager, AC ^{[1
]}

机构：

[1] Simon Fraser Univ, Dept Chem, Burnaby, BC V5A 1S6, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 10期

关键词：

D O I：

10.1021/jo9820871

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of(+)-disparlure, 1, the sex pheromone of gypsy moth (Lymantria dispar), commenced from cis-vinyl epoxide 4 which was prepared by our asymmetric chloroallylboration in 99% de and 94% ee. Hydroboration of 4 using dicyclohexylborane in THF, followed by sodium perborate oxidation gave a crystalline cis-3,4-epoxy alcohol 3 whose enantiomeric purity was enhanced by recrystallization. Conversion of 3 to (+)-disparlure was via alkylation of the tosylate. (+)-Disparlure was produced in four steps with an overall yield of 27% and greater than or equal to 99.5% ee.

引用

页码：3719 / 3721

页数：3

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