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PubMed · 10959583

Synthesis of decalin type chiral synthons based on enzymatic function.

M Nozawa·Y Murakami·K Noda·R Tamatsukuri·K Kato·H Akita
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Abstract

Enzymatic monobenzoylation of (+/-)-2-hydroxy-decahydro-5,5,8a-trimethyl-1-naphthalenemethano l derivatives (1-4) using vinyl benzoate in organic solvent gave the optically active diols (1-4) and monobenzoates (16-19). The enantiomeric excess (ee) of the enzymatic reaction products were found to be in the range of 11% to 49%. On the other hand, enzymatic hydrolysis of the acetoxybenzylidene acetal (+/-)-25d, e was found to give more than 90% ee of (10aS)-25d, e in moderate yield. Finally, the 90% ee of (10aS)-25e was converted to the 90% ee of the desired (8aS)-1.

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EnzymesHydrolysisNaphthalenesSpectrum AnalysisStereoisomerismJournal ArticleResearch Support, Non-U.S. Gov't

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M Nozawa, Y Murakami, K Noda, R Tamatsukuri, K Kato, H Akita. 2000. Synthesis of decalin type chiral synthons based on enzymatic function.. https://doi.org/10.1248/cpb.48.1176

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