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Synthesis of syn-4,6-dimethyldodecanal, the male sex pheromone and trail-following pheromone of two species of the termite Zootermopsis

par Ghostin, Jean ;Bordereau, Christian;Braekman, Jean Claude
Référence Natural product research, 25, 5, page (560-568)
Publication Publié, 2011-03

Article révisé par les pairs

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Résumé :

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. © 2011 Taylor & Francis.