Synthesis and gas chromatographic separation of the eight stereoisomers of diprionol and their acetates, components of the sex pheromone of pine sawflies

The present report describes syntheses of the eight possible stereoisomers of 3,7-dimediyl-2-pentadecanol 1, and the corresponding acetates. The latter are components of the sex pheromone of the Neodiprion, Diprion and Gilpinia genera (Diprionidae). Synthetic intermediates were prepared from either chiral starting materials or by asymmetric syntheses. The stereochemical compositions of the isomeric diprionols were determined by using capillary gas chromatography on tandem column systems, some with chiral phase coatings.