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

Chemo-enzymatic synthesis of drimane-8α,11-diol from farnesol derivatives using a terpene cyclase from Bacillus megaterium was 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 was achieved. Among farnesol derivatves, MOM protected farnesol was found to be a superior substrate to other farnesol derivatives. The resulting drimane derivative was easily converted to the target natural product in one step.