Enantioselectivity in the Biotransformation of Bicyclo[3.1.1]heptanes with the Cultured Cells of Nicotiana tabacum
- 5 March 1987
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 16 (3) , 471-474
- https://doi.org/10.1246/cl.1987.471
Abstract
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.Keywords
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