An efficient and convenient synthesis of enantiopure 4-(t-butyldimethylsilyloxy)-cyclohex-2-en-1-one: a formal synthesis of (±)-mesembranol

Inexpensive enantiopure (+)-limonene oxide 1 is converted to 4-(R)-(t-butyldimethylsilyloxy)-cyclohex-2-en-1-one 2a. All isolated intermediates can be distilled obviating the need for chromatography. With 2a,b in hand, a formal synthesis of (±)-mesembranol 17 using vinyl triflate methodology is high yielding.