Chiral & / #945 / -hydroxy and & / #945 / -acetoxy enones are important starting materials in the synthesis of many biologically active materials. In this work, enantiomerically pure & / #947 / -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. & / #945 / ' / -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 & / #945 / ' / -acetoxy enone and & / #945 / ' / -hydroxy enone is obtained. In this stage, for the screening of the reaction many enzymes were tried. Reduction of & / #945 / ' / -hydroxy enone furnished enantiopure & / #947 / -hydroxy enone.
| Identifer | oai:union.ndltd.org:METU/oai:etd.lib.metu.edu.tr:http://etd.lib.metu.edu/upload/1116383/index.pdf |
| Date | 01 January 2004 |
| Creators | Findik, Hamide |
| Contributors | Demir, Ayhan Sitki |
| Publisher | METU |
| Source Sets | Middle East Technical Univ. |
| Language | English |
| Detected Language | English |
| Type | M.S. Thesis |
| Format | text/pdf |
| Rights | To liberate the content for public access |
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