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Microbially-aided preparation of (S)-2-Methoxycyclohexanone key intermediate in the synthesis of Sanfetrinem

✍ Scribed by Claudio Fuganti; Piero Grasselli; Monica Mendozza; Stefano Servi; Gioia Zucchi

Book ID: 104207504
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 393 KB
Volume: 53
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(96)01152-0

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✦ Synopsis

2-Methoxycyclohexanone l, useful intermediate in the synthesis of Sanfetrinem 2, is obtained from (S) ct-benz'ylidene cyclohexanol 4, derived from the ketone 3 through a short sequence involving as key step yeast reduction of the carbonyl group. The (R) enantiomer of I is similarly accessible from the (R) enantiomer of 4 obtained either upon Candida lipolytica-mediated reduction of 3 or from (R,S)-4 by porcine pancreatic lipase catalyzed acetylation with vinyl acetate. Also the saturated carbinols 7 and 8, which accompany 4 in the microbial reduction of 3, are converted into l through unexceptional steps. Nocardia opaca, Pichia etchelsii and Mucor subtilissimus provide from 3 upon reduction (S)-configurated 4, 7 and 8 possessing moderate-high ee values.

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