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.
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页码：2063 / 2070
页数：8
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