Epoxide hydrolases bisabolol

Scheme 15. Chemoenzymatic synthesis of a-bisabolol using fungal epoxide hydrolase...

Chen, X.-J., Archelas, A. and Furstoss, R. (1993) Microbiological transformations. 27. The first examples for preparative-scale enantioselective or diasteieoselective epoxide hydrolases using microorganisms. An unequivocal access to all four bisabolol stereoisomers. /. Org. Chem., 58, 5528-5532. 

An application of microbial epoxide hydrolases for the synthesis of a-bisabolol, one of the stereoisomers (out of four) of interest for the cosmetic industry, is illustrated in Scheme 17. This approach was based on the diastereoselective hydrolysis of a mixture of oxirane diastereoisomers obtained by chemical synthesis from (/ )- or (5-limonene [130]. Thus, starting from (S)-limonene, the biohydrolysis of the mixture of (4S,8i S) epoxides... 

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