Abstract
A simple transformation of terpinen-4-ol (1) to dihydropinol (4) is described. S-Terpinen-4-ol was stereospecifically oxidized with vanadyl diacac to cis-terpinen-4-ol-epoxide (2). Reduction with LiAlD4 afforded the unexpected 1R-deutero-2S,4S-dihydroxy menthane (3) which was cyclized in acid to 4.