ChemInform Abstract: Microbially-Aided Preparation of (S)-2-Methoxycyclohexanone Key Intermediate in the Synthesis of Sanfetrinem.

✍ Scribed by C. FUGANTI; P. GRASSELLI; M. MENDOZZA; S. SERVI; G. ZUCCHI

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 33 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199726265

✦ Synopsis

Microbially-Aided Preparation of (S)-2-Methoxycyclohexanone Key Intermediate in the Synthesis of Sanfetrinem.

-It is shown that the enantiomerically pure (S)-carbinol (I), obtained by baker's yeast-mediated reduction of 2-benzylcyclohexanone, can be transformed efficiently into the title ketone (S)-(IV). Formation of ( S)-(I) is also possible with other microorganisms but with lower chemoand enantioselectivity. However, the accompanied alcohols (VI) and (VII) can also be converted into the desired ketone (S)-(IV). Interestingly, resolution of the ketone (V) with candida lipolytica yields the (R)-enantiomer of (I) which is also accessible via PPL-mediated acylation of the racemic ether (III).