SYNTHESES OF THE FEMALE SEX-PHEROMONES OF MATSUCOCCUS PINE SCALES USING THE [2,3]-WITTIG REARRANGEMENT OF A BISALLYLIC TERTIARY ETHER

被引：5

作者：

SHI, XW ^{[1
]}

WEBSTER, FX ^{[1
]}

MEINWALD, J ^{[1
]}

机构：

[1] CORNELL UNIV,DEPT CHEM,ITHACA,NY 14853

来源：

TETRAHEDRON | 1995年 / 51卷 / 38期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

D O I：

10.1016/0040-4020(95)00622-F

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convergent, general synthesis of (2E,4E)-4,6,10,12-tetramethyltrideca-2,4-dien-7-one (matsuone, 1) and five closely related analogs (2-6), which serve as sex pheromone components of female Matsucoccus pine scales, is described. The aldehydes 8a and 8b were obtained via a reaction sequence in which the key step is a [2,3]-Wittig sigmatropic rearrangement of the oxazoline ether of bisallylic tertiary alcohol 11. Coupling of 8 with the appropriate nucleophilic reagents, followed by oxidation of the resultant secondary alcohols, afforded the pheromone components 1-6.

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收藏

页码：10433 / 10442

页数：10

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