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Enzyme-triggered opening of an epoxide: Chemoenzymatic synthesis of (2R,5R)- and (2S,5R)-pityol

✍ Scribed by Martin Mischitz; Alexandra Hackinger; Iris Francesconi; Kurt Faber

Book ID: 104203237
Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 250 KB
Volume: 50
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)85340-0

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✦ Synopsis

Treatment of a diastereomeric mixture of W-epoxy-ester 1 with a crude immobilised enzyme preparation (Novo SP 409) or whole lyophilized cells of Rhodococcu.s eryfhropolis NCIB 11540 in aqueous buffer (pH 7.0) did not lead to the formation of the expected epoxy alcohol 2 or diol5 but surprisingly furnished the rearranged products 4a and 4b in 98% enantiomeric excess. (2R*,SR*)-2-(1-Hydroxy-1-methylethyl)-5-methyltetrahydrofuran (pityol, 4a) is a pheromone of

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