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Chemoenzymatic synthesis of 4-hydroxy enones

Köse, Elif
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 a̕-acetoxy-a-methyl and ?-hydroxy-a-methyl cyclic enones starting from a-methyl-β-methoxy cyclic enone is described. Manganese (III) acetate-mediated acetoxylation followed by the enzyme-mediated hydrolysis of a̕-acetoxy enone provides acetoxy enones. The reduction of the hydroxy enone, obtained from hydrolysis, furnished both enantiomers of 4-hydroxy enone or ?-hydroxy enone by using LiAlH4. This study is a model for the synthesis of these type compounds.