Synthesis of Drimane-8α,11-diol Using Terpene Cyclase from Bacillus Megaterium

Abstract

Chemo-enzymatic synthesis of drimane-8α,11-diol from farnesol derivatives using a terpene cyclase from Bacillus megaterium is achieved. Farnesol was not suitable for enzymatic transformation. On the other hand, farnesol derivatives in which the hydroxy group is protected with a conventional protecting group underwent cyclization to give the corresponding drimane-8α,11-diol derivatives. One of the cyclized products was transformed into 1 under mild conditions. Chemo-enzymatic synthesis of drimane derivatives from farnesol derivatives are achieved. Among farnesol derivatves, MOM protected farnesol was found to be superior substrate to other farnesol derivatives. The resulting drimane derivatives are easily converted to the target natural product in one step.