Enantiodivergent Route to the Aromatic Bisabolane Sesquiterpenes via a Chiral Acetylene Alcohol

Efficient preparation and practical utilization of (R)-1-benzyloxy-3-butyn-2-ol have been established. Treatment of (2S,3S)-4-benzyloxy-2,3-epoxybutyl chloride, obtained via the Sharpless epoxidation, with n-butyllithium afforded (R)-1-benzyloxy-3-butyn-2-ol which could be transformed enantiodivergently into the key synthetic intermediates of the aromatic bisabolane sesquiterpenes.