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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 20, 1990 - Issue 3
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Original Articles

Stereoselective Synthesis of a Potential Sex Pheromone of Stenoma Cecropia (Lepidoptera)

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Pages 333-344 | Received 18 Sep 1989, Published online: 24 Oct 2006
 

Abstract

A convenient preparation of (Z, E) 9, 11-and (Z, Z) 9, 11-tetradecadien-1-yl and (9Z) 9, 11-tetradecenyn-1-yl acetate, alcohol and aldehyde with 99.5 % stereoisomeric purity is described. The key step of this synthesis is the carbocupration of acetylene followed by palladium catalyzed cross coupling reaction with the appropriate zinc reagent.

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