Regioselective reduction of keto groups in Michael adducts of levoglucosenone and cyclohexanone

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.