Stereospecific synthesis of -(-)--verbenol and its antipode by inversion of sterically hindered alcohols.

-(-)--Verbenol () and its antipode, -(+)--verbenol () have been confirmed as the critical pheromone components of bark beetles. Synthesis of these two active secondary alcohols ( and ) from commercially available starting materials --pinene and --pinene was reported. The key steps were mainly depended on the effective S2 stereo-inversion of the hydroxy group of sterically hindered alcohols ( and '), using Mitsunobu reaction or hydrolysis of mesylate ester, alternatively. Our results provide a new and stereo-selectivity way to obtain optically active insect pheromones.