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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 24, 1994 - Issue 16
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Original Articles

A Short and Efficient Synthesis of (3E,5Z)-1,3,5-Undecatriene from (1E)-1-Chloro-1,3-butadiene

Chanh Huynh Laboratoire de Chimie, Ecole Normale Supérieure, 24, Rue Lhomond 75231, Paris, Cedex, 05, France
,
Mou[acaron]d Alami Laboratoire de Chimie, Ecole Normale Supérieure, 24, Rue Lhomond 75231, Paris, Cedex, 05, France
&
Gérard Linstrumelle Laboratoire de Chimie, Ecole Normale Supérieure, 24, Rue Lhomond 75231, Paris, Cedex, 05, France
Pages 2273-2280 | Received 10 Feb 1994, Published online: 23 Sep 2006
 
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Abstract

A short synthesis of (3E,5Z)-1,3,5-undecatriene (cis-galbanolene) is described. The key step is the Pd/Cu-catalyzed coupling reaction of (E)-1-chloro-1,3-butadiene with 1-alkynes followed by stereoselective zinc reduction of the triple bond.

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