Keywords
cyclohexanone
Ketones
levoglucosenone
Michael adduct
regioselective reduction
Abstract
Conditions for the highly regioselective reduction of the specified keto groups in the Michael adduct of levoglucosenone and cyclohexanone have been developed. Selective reduction of the keto group in the cyclohexanone moiety was performed under the action of lithium metal in NH3/THF system. Reduction of the keto group in the carbohydrate residue was accomplished microbiologically or by refluxing with NaBH(OAc)3 in benzene.
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