Chiral cyclic polyoxo-ketones are important structural units in many natural products, biologically active compouds, such as prostaglandins, didemnenones, sarkomycin, punaglandin, clavulone, etc. In this work, a chemoenzymatic synthesis of both enantiomers of the &amp / #945 / &rsquo / -acetoxy-&amp / #945 / -methyl and &amp / #947 / -hydroxy-&amp / #945 / -methyl cyclic enones starting from &amp / #945 / -methyl-&amp / #946 / -methoxy cyclic enone is described. Manganese (III) acetate-mediated acetoxylation followed by the enzyme-mediated hydrolysis of &amp / #945 / &rsquo / -acetoxy enone provides acetoxy enones. The reduction of the hydroxy enone, obtained from hydrolysis, furnished both enantiomers of 4-hydroxy enone or &amp / #947 / -hydroxy enone by using LiAlH4. This study is a model for the synthesis of these type compounds