Enantioselective chemoenzymatic synthesis of oseltamivir (tamiflu)(r) intermediates

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2008
Eşiyok, Hacı
The objective of this presented study was to synthesize optically active compounds considered to be key intermediates in the synthesis of Oseltamivir (Tamiflu) by performing chemical and biotechnological methods. Thereof, the carboethoxy cyclohexenone skeleton first was synthesized utilizing easily available substances. The synthesis of alpha-hydroxy ketones in enantiomerically pure form offers a great importance in the synthesis of biologically active compounds. Toward this fact, the enantioselective synthesis of alpha-hydroxy carboethoxy cyclohexenone scaffold has been accomplished by following the routes which were manganese(III) acetate-mediated chemical oxidation followed by enzyme-mediated hydrolysis and additionally microbial direct biooxidation by whole cells of fungi expressly A. oryzae and A. flavus. A very satisfying results have been obtained by both of the methods.

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Citation Formats
H. Eşiyok, “Enantioselective chemoenzymatic synthesis of oseltamivir (tamiflu)(r) intermediates,” M.S. - Master of Science, Middle East Technical University, 2008.