A Chemoenzymatic Synthesis of the Sex Pheromone of Lasioderma serricorne F.

a short and efficient preparation of enantiomerically enriched (80% ee) (-)-serricornine (1), the sex pheromone of the cigarette beetle lasioderma serricorne f., was developed in 8 steps and 13% overall yield from methyl (r)-3-hydroxypentanoate readily prepared by baker's yeast reduction of methyl 3-oxopentanoate in the presence of allyl alcohol as enzyme inhibitor.