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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 18
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Original Articles

Straightforward Preparation of (2E,4Z)-2,4-Heptadien-1-ol and (2E,4Z)-2,4-Heptadienal

Pages 3233-3241 | Received 18 Mar 2003, Published online: 17 Aug 2006
 

Abstract

A concise synthesis of (2E,4Z)-2,4-heptadien-1-ol and (2E,4Z)-2,4-heptadienal is presented. Commercially available (Z)-2-penten-1-ol was converted to ethyl-(2E,4Z)-2,4-heptadienoate by reaction with activated MnO2 and (carboethoxymethylene)triphenylphosphorane in the presence of benzoic acid as a catalyst. Ethyl-(2E,4Z)-2,4-heptadienoate was converted to (2E,4Z)-2,4-heptadien-1-ol with LiAlH4. The alcohol was partially oxidized to (2E,4Z)-2,4-heptadienal with MnO2. The title compounds are male-specific, antennally active volatile compounds from the Saltcedar leaf beetle, Diorhabda elongata Brulle (Coleoptera: Chrysomelidae) and have potential use in the biological control of the invasive weed saltcedar (Tamarix spp).

Acknowledgments

I thank Bruce W. Zilkowski and Robert J. Bartelt for acquiring mass spectral data, David Weisleder for acquiring NMR spectra, and Robert J. Bartelt for helpful discussions.

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