Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
Enantioselectivity in the Biotransformation of Bicyclo[3.1.1]heptanes with the Cultured Cells of Nicotiana tabacum
Takayuki SugaHiroki HamadaToshifumi Hirata
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1987 Volume 16 Issue 3 Pages 471-474

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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.

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