Synthesis of (1S,2S,6S,10R)- and (1S,2R,6R,10R)-1,2,6,10-Tetramethyldodecyl Propanoate, the Components of the Sex Pheromone of the Pine Sawfly,Microdiprion pallipes

(1S,2S,6S,10R)- and (1S,2R,6R,10R)-1,2,6,10-tetramethyldodecyl propanoate (1 and 2), the components of the pheromone of Microdiprion pallipes, were synthesized from two chiral and nonracemic building blocks, (R)-3-tert-butoxycarbonyl-2-methylpropanoic acid (D) and (2R,6S)-7-acetoxy-2,6-dimethyl-1-heptanol (G), by employing lipase-catalyzed kinetic resolution in a later step.