The Journal of Organic Chemistry

Silicon-mediated skipped diene synthesis. Application to the melon fly pheromone

SR Wilson, PA Zucker

Index: Wilson, Stephen R.; Zucker, Paul A. Journal of Organic Chemistry, 1988 ,  vol. 53,  # 20  p. 4682 - 4693

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Citation Number: 42

Abstract

The 1, l-diene unit is a key structural feature of many fatty acid derived natural products including arachidonic acid, several of the leukotrienes, and a variety of insect pheromones. In this paper substituted [2-[(tri-methylsilyl) methyl] cyclopropyl] carbinols are demonstrated to cleave readily, upon treatment with acid or upon conversion to the corresponding mesylates, to give mono-and disubstituted 1, l-pentadienes. Stereoselective formation of ...