Lactones 26 : Stereoselective microbial epoxidation of unsaturated bicyclic γ-lactones with the alkylsubstituted cyclohexane system

The strain Absidia cylindrospora was chosen among eight fungal strains for the biotransformation of unsaturated lactones 1a–c. The processes were carried out by means of shaken cultures. The compounds 1a and 1b were efficiently converted into the corresponding trans-epoxylactones (2a and 2b), whereas the transformation of 1c gave the unsaturated hydroxylactone 3, with the tertiary hydroxy group introduced in the allylic position. The compound 2b was obtained with 100% ee. The structures of compounds 2a and 2b were fully confirmed by the X-ray analysis, which showed the half boat and half chair conformation of cyclohexane ring in these molecules, respectively. All the products were not reported previously in the literature.