Mikrobial Oxidation in Synthesis: Preparation of (+)- and (-)-Pinitol from Benzene

Article abstract of DOI:10.1016/S0040-4020(01)81025-5

Microbial oxidation with Pseudomonas putida of benzene affords cis-1,2-dihydroxycyclohexa-3,5-diene (2) which may be converted in five steps and 49percent overall yield to (+/-)-pinitol.Resolution of an intermediate alcohol (6) with menthoxyacetyl chloride provides optically pure materials which may be independently transformed to (+)- or (-)-pinitol.Demethylation conditions for pinitol together with further reactions of (2) and related compounds were investigated.