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

Abstract

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_N2 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.

Keywords:

• S-(−)-trans-verbenol
• R-(+)-trans-verbenol
• sterically hindered alcohols
• Mitsunobu reaction
• S_N2 inversion

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

The work was financially supported by the Beijing Natural Science Foundation (6194044), the National Natural Science Foundation of China (31901320), and the Institute Special Fund for Basic Research, Institute of Forest Ecology, Environment, and Protection, Chinese Academy of Forestry (CAFYBB2016SY017).