Chemoenzymatic synthesis of (S)-(-)-frontalin using bacterial epoxide hydrolases

Article abstract of DOI:10.1055/s-1997-1153

The pheromone (S)-(-)-frontalin (1) was synthesized in five steps in 94percent ee via a chemoenzymatic route. In the key step, 2-methyl-2-(pent-4-enyl)oxirane [(±)-7a] was resolved employing lyophilized cells of Rhodococcus equi IFO 3730 (E = 39).