Microbiological transformations. 30. Enantioselective hydrolysis of racemic epoxides: the synthesis of enantiopure insect juvenile hormone analogs (bower's compound)

Abstract The enantioselective epoxide biohydrolysis of the racemic benzodioxole 6,7-epoxygeraniol derivative 1 has been achieved using the fungus A. niger . This new type of preparative scale bioconversion allows the synthesis of both enantiomers of Bower's compound, an analogue of insect juvenile hormone. Biological tests showed that the 6(R) enantiomer was about ten times more active than the 6(S) enantiomer against the yellow meal worm Tenebrio molitor .