Chemoenzymatic synthesis of chiral hydroxymethyl cycloalkenols

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2004

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Şenocak, Deniz

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Chiral cyclic alkenols with hydroxymethyl functionality are important structural units in many biologically active natural compouds such as prostaglandins, sesquiterpene antiviral agents, pentenomycins, xanthocidin, sarkomycin, etc. 1,3-cycloalkanediones are converted into bicyclic polyoxo derivatives with formaldehyde and trioxane in the presence of Lewis acid. Selective oxidation of the bicyclic compounds by using manganese(III)acetate followed by enzyme-catalyzed kinetic resolution afforded chiral bicyclic hydroxy ketones. Reduction of carbonyl group and cleavage of the ether functionality furnished the desired chiral cycloalkanols with hydroxymethyl group. This study is a model for the synthesis of these type of compounds.

Subject Keywords

Chemistry, Organic

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http://etd.lib.metu.edu.tr/upload/12605056/index.pdf
https://hdl.handle.net/11511/14145

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Graduate School of Natural and Applied Sciences, Thesis

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Citation Formats

D. Şenocak, “Chemoenzymatic synthesis of chiral hydroxymethyl cycloalkenols,” M.S. - Master of Science, Middle East Technical University, 2004.