Stereoselective synthesis of the obscure mealybug pheromone by hydrogenation of a tetrasubstituted alkene precursor |
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| Authors: | Yunfan Zou Jocelyn G Millar |
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| Institution: | Department of Entomology, University of California, Riverside, CA 92521, USA |
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| Abstract: | An improved diastereoselective synthesis of (1R∗,2R∗,3S∗)-1-acetoxymethyl-2,3,4,4-tetramethylcyclopentane 1, the sex pheromone of the obscure mealybug, Pseudococcus viburni, is described. The key step was diastereoselective catalytic hydrogenation of the tetrasubstituted double bond in 2,3,4,4-tetramethyl-cyclopent-2-enone 4 to give the thermodynamically less favored cis-2,3,4,4-tetramethyl-cyclopentanone 3a. |
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| Keywords: | Pheromone Monoterpenoid Diastereoselective synthesis Catalytic hydrogenation |
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