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

Abstract

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.

Keywords

• (-)-serricornine
• pheromone
• synthesis
• S. cerevisiae