Diastereoselective synthesis of dihydropyrans via Prins cyclization of enol ethers: total asymmetric synthesis of (+)-civet cat compound.

ABSTRACT

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) can be efficiently used for Prins cyclization of acrylyl enol ethers to 5,6-dihydro-2H-pyran-2-acetates stereo- and regioselectively in good yields. The methodology was used for the total synthesis of natural product (+)-civet.