6533b7d1fe1ef96bd125d872
RESEARCH PRODUCT
Synthesis of syn-4,6-dimethyldodecanal, the male sex pheromone and trail-following pheromone of two species of the termite Zootermopsis.
Jean Claude BraekmanJean GhostinChristian Bordereausubject
Malefood.ingredientbiologyMolecular StructureStereochemistryChemistryZootermopsisOrganic ChemistryTermopsidaeIodine CompoundsPlant ScienceIsopterabiology.organism_classificationBiochemistryZootermopsis nevadensisGas Chromatography-Mass SpectrometryPheromonesAnalytical ChemistryfoodZootermopsis angusticollisIsomerismSex pheromoneValeratesPheromoneAnimalsdescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2011-03-01 | Natural product research |