An easy and versatile approach to the synthesis of chiral pheromone lactones via 4,4-dimethyl-2-oxazoline derivatives

被引：17

作者：

Zarbin, PHG ^{[1
]}

Oliveira, ARM ^{[1
]}

Simonelli, F ^{[1
]}

Villar, JAFP ^{[1
]}

Delay, O ^{[1
]}

机构：

[1] Univ Fed Parana, Dept Quim, BR-81531990 Curitiba, Parana, Brazil

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 40期

关键词：

pheromones; synthesis; chiral lactones; oxazoline;

D O I：

10.1016/j.tetlet.2004.08.083

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

As part of our ongoing investigation on the versatility of 4,4-dimethyl-2-oxazoline derivatives, we present a straightforward synthesis of chiral lactone pheromones from readily available starting materials. As an application, we describe the diastereoselective synthesis of cis and traps-2-methyl-5-hexanolide (1), a pheromone component of the carpenter bee Xylocopa hirutissima, and a formal synthesis of (4R,5Z)-5-tetradecen-4-olide (2), the sex pheromone of the Japanese beetle Popillia japonica. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：7399 / 7400

页数：2

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