Chemoenzymatic functionalization of cyclic 1,3-diketones

Date

2004

Author

Fındık, Hamide

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Chiral a-hydroxy and a-acetoxy enones are important starting materials in the synthesis of many biologically active materials. In this work, enantiomerically pure ?-hydroxy enone and polyoxo cyclohexenones are synthesized starting from 1,3-cyclohexandione. In the first step, 1,3-cyclohexandione is protected under acid catalyzation and 3-methoxy-2-methyl-2-cyclohexen-1-one is obtained. a'-Acetoxy enone is obtained by Mn(OAc)3 mediated oxidation which is an attractive alternative to other multi-step procedures in the literature. Enzymatic kinetic resolution is applied to the racemic form of this product and enantiomerically pure a'-acetoxy enone and a'-hydroxy enone is obtained. In this stage, for the screening of the reaction many enzymes were tried. Reduction of a'-hydroxy enone furnished enantiopure ?-hydroxy enone.

Subject Keywords

Carbonyl compounds., Chemistry, Organic

URI

http://etd.lib.metu.edu/upload/1116383/index.pdf
https://hdl.handle.net/11511/13905

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Graduate School of Natural and Applied Sciences, Thesis

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Citation Formats

H. Fındık, “Chemoenzymatic functionalization of cyclic 1,3-diketones,” M.S. - Master of Science, Middle East Technical University, 2004.