Highly efficient synthesis of (+/-)-lamoxirene, the gamete-releasing and gamete-attracting pheromone of the Laminariales (Phaeophyta)

被引：12

作者：

Hertweck, C ^{[1
]}

Boland, W ^{[1
]}

机构：

[1] UNIV BONN,KEKULE INST ORGAN CHEM & BIOCHEM,D-53121 BONN,GERMANY

来源：

TETRAHEDRON | 1997年 / 53卷 / 43期

关键词：

D O I：

10.1016/S0040-4020(97)01008-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and highly diastereoselective synthesis of lamoxirene (cis-2-cyclohepta-2,5-dienyl-3-vinyloxirane, 4), the gamete releasing and -attracting pheromone of the Laminariales (Phaeophyceae), is reported. Ethyl cyclohepta-2,5-diene carboxylate (7) is effectively alkylated to provide the syn-alpha-chlorohydrin 8 via reductive chloroallylboration with DIBAL-H and (Z)-gamma-chloroallyl-BBN. Cyclisation of the chlorohydrin 8 is readily achieved with DBU yielding the pheromone in 25% overall yield from the cyclopropyl ester 5. (C) 1997 Elsevier Science Ltd.

引用

页码：14651 / 14654

页数：4

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