Mori, K., & Tabata, J. 2017 Pheromone synthesis. Part 262: Determination of the absolute configuration of the female sex pheromone [(1S,2S)-(-)-(1,2-dimethyl-3-methylenecyclopentyl) acetaldehyde] of the pineapple mealybug (Dysmicoccus brevipes) by synthesis coupled with X-ray analysis. Tetrahedron 73: 6530-6541
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Notes: The enantiomers of (anti-1,2-dimethyl-3-methylenecyclopentyl)acetaldehyde, one of which is the female sex pheromone of the pineapple mealybug (Dysmicoccus brevipes), were synthesized. Chirality was introduced by means of lipase-catalyzed asymmetric acetylation of (±)-2,3-dimethyl-2-cyclopenten-l-ol. X-ray analysis of (-)-camphanate ester of (1S,2S)-(-)-2-(1,2-dimethyl-3-methylenecyclopentyl) ethanol confirmed its (1S,2S)-absolute configuration. The natural pheromone was identified with the (1S,2S)-aldehyde by comparing the specific rotation, enantioselective GC retention time and pheromone activity.
