Enantioselectivity in the Biotransformation of Bicycloheptanes with the Cultured Cells of Nicotiana tabacum

Article abstract of DOI:10.1246/cl.1987.471

The biotransformation of the enantiomeric pairs of bicyclo<3.1.1>heptane derivatives with the cultured cells of Nicotiana tabacum was investigated.The hydrogenation of the C-C double bond of verbenone took place enantioselectively in preference of the (1S,5S)-enantiomer and the hydrogen attack occurred stereospecifically from the re-face at its C-2.The oxidation of the hydroxyl group of neoisopinocampheol occurred enantioselectively in preference of the (1S,2S,3R,5R)-enantiomer, whereas such an enantioselective oxidation was not the case for neoisoverbanol.