| Abstract
| - The synthesis of serricornin [(4S,6S,7S)-7-hydroxy-4,6-dimethylnonan-3-one], a sex pheromone produced by thefemale cigarette beetle (Lasioderma serricorne F.), in sevensteps from readily available racemic 1,4-dioxa-8-thiaspiro[4.5]decane-6-carboxaldehyde (6) is described. The key stepsinclude enantioselective aldol reaction of 6 with tetrahydrothiopyran-4-one catalyzed by 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole to fabricate the tetrapropionate skeleton, stereoselective LisBu3BH reduction of the resulting aldol adduct,Barton−McCombie deoxygenation, and Raney nickel desulfurization.
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