Synthesis of syn-4,6-dimethyldodecanal, the male sex pheromone and trail-following pheromone of two species of the termite Zootermopsis |
| |
Authors: | Ghostin J Bordereau C Braekman J C |
| |
Institution: | Department of Organic Chemistry, CP 160/06, Faculty of Sciences, University of Brussels, 50 Avenue F. Roosevelt, 1050 Brussels, Belgium. |
| |
Abstract: | Recently, we reported that syn-4,6-dimethyldodecanal is the male sex pheromone and the trail-following pheromone of the Termopsidae Zootermopsis nevadensis and Zootermopsis angusticollis. In this article, we describe the syntheses of the mixture of the four stereoisomers of 4,6-dimethyldodecanal using a synthetic pathway where the key step is a Wittig reaction between methyl 4-methyl-5-oxo-pentanoate and 1-methylheptyl-triphenylphosphonium iodide, and of (±)-syn-4,6-dimethyldodecanal starting from 3,5-dimethyl-2-cyclohexen-1-one. Direct GC-MS comparison of these synthetic samples with the natural pheromone allowed its unambiguous identification. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|