Enantioselective synthesis of (2R,3R,7S)-3,7 -dimethylpentadecan-2-ol, sex pheromone component of pine sawflies

The pine sawfly, Neodiprion sertifer (Geoffrey) (Hymenoptera: Diprionidae), is a widespread and economically important forest insect in North America, Japan and Europe. It has been demonstrated that the main sex pheromone components of this species are acetate or propionate of 3,7-dimethyl-2-pentadecanol (diprionol). We describe herein an enantioselective synthesis of (2R,3R,7S)-diprionol in 12 steps (7.5% overall yield), starting from commercial (-)-isopulegol.