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S -(−)- trans -Verbenol ( 1 ) and its antipode,  R -(+)- trans -verbenol ( 1′ ) have been confirmed as the critical pheromone components of bark beetles. Synthesis of these two active secondary alcohols ( 1  and  1′ ) from commercially available starting materials  S - α -pinene and  R - α -pinene was reported. The key steps were mainly depended on the effective S N 2 stereo-inversion of the hydroxy group of sterically hindered alcohols ( 3  and  3 ′), using Mitsunobu reaction or hydrolysis of mesylate ester, alternatively. Our results provide a new and stereo-selectivity way to obtain optically active insect pheromones.

Stereospecific synthesis of S -(−)- trans -verbenol and its antipode by inversion of sterically hindered alcohols