Synthesis of (+)‐Artemeseole

The synthesis of the monoterpene (+)‐artemeseole ( 1b ) is accomplished by starting from (Z)‐dienol 5 . Sharpless epoxidation of 5 gives oxirane 4 . Attempted opening of the epoxide ring in 4 or in derivatives 8a, b by various allyl or acetylide anions gives side reactions, but the desired coupling with a C 3 unit is achieved in the reaction of silyl‐protected oxirane 8b with 9 or 13 giving 17 and 19a , respectively. Alkenol 19a is further converted into oxirane 21 by desilylation, tosylation, and base‐induced epoxide formation. Anion generation from 21 by reductive desulfurization yields (dialkenylcyclopropyl)methanol 3 . Acid‐catalyzed cyclization to a tetrahydrofuran completes the synthesis of 1b .