Chemoenzymatic synthesis of 4-hydroxy enones

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2004

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Köse, Elif

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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.

Subject Keywords

Carbonyl compounds., Chemistry, Organic

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http://etd.lib.metu.edu.tr/upload/1252519/index.pdf
https://hdl.handle.net/11511/13906

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Graduate School of Natural and Applied Sciences, Thesis

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Citation Formats

E. Köse, “Chemoenzymatic synthesis of 4-hydroxy enones,” M.S. - Master of Science, Middle East Technical University, 2004.