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The gross structure of the sex pheromone produced by female cigarette beetle was established as 4,6-dimethyl-7-hydroxynonan-3-one (a trivial name; serricornin) by the spectroscopic evidences1> and the synthesis of their stereoisomeric mixture.2) In the serricornin molecule, three chiral carbons at C4, C6 and C7 indicated the existence of eight possible stereoisomers which could devide into (6,7)j/zreo-serricornins and (6,l)-erythro-sQmcornins by the relative configuration at C6methyl and C7-hydroxy groups. Recently, the absolute configuration at C6 and C7 of the naturally occurring serricornin was established as (6S,7S)-threo by stereoselective syntheses of (4RS,6R,1S)-erythro-sQrricornin3) and (4RS,6R,7R)-threo-serncomin4) from L-(+)-tartaric acid and (2S,3S)-3methylaspartic acid, respectively.

The pheromone activity of (.+-.)-serricornins for male cigarette beetle (Lasioderma serricorne F.)