Stereoselective synthesis of (+)-sordidin, the male-produced aggregation pheromone of the banana weevil Cosmopolites sordidus

被引：9

作者：

Yadav, J. S. ^{[1
]}

Reddy, K. Bhaskar ^{[1
]}

Prasad, A. R. ^{[1
]}

Rehman, H. Ur ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON | 2008年 / 64卷 / 09期

关键词：

banana weevil; Jacobsen's resolution; epoxide opening; intramolecular acetalization;

D O I：

10.1016/j.tet.2007.12.051

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereoselective synthesis of (1S,3R,5R,7S)-(+)-sordidin, the natural male-produced aggregation pheromone of the banana weevil Cosmopolites sordidus (Germar) starting from 5-benzyloxy-(2E)-pentene-1-ol is described. The key transformations employed in the synthesis are Sharpless asymmetric epoxidation, Ueno - Stork cyclization, and Jacobsen kinetic resolution. (c) 2007 Published by Elsevier Ltd.

引用

页码：2063 / 2070

页数：8

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