| Title: | "Synthesis of syn-4,6-dimethyldodecanal, the male sex pheromone and trail-following pheromone of two species of the termite Zootermopsis" |
| Author(s): | Ghostin J; Bordereau C; Braekman JC; |
| Address: | "Department of Organic Chemistry, CP 160/06, Faculty of Sciences, University of Brussels, 50 Avenue F. Roosevelt, 1050 Brussels, Belgium" |
| DOI: | 10.1080/14786419.2010.535152 |
| ISSN/ISBN: | 1478-6427 (Electronic) 1478-6419 (Linking) |
| 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: | Animals Gas Chromatography-Mass Spectrometry Iodine Compounds/chemistry Isomerism Isoptera/*chemistry Male Molecular Structure Pheromones/*chemical synthesis Valerates/chemistry; |
| Notes: | "MedlineGhostin, J Bordereau, C Braekman, J C eng England 2011/03/11 Nat Prod Res. 2011 Mar; 25(5):560-8. doi: 10.1080/14786419.2010.535152" |
