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 & / #945 / &rsquo / -acetoxy-& / #945 / -methyl and & / #947 / -hydroxy-& / #945 / -methyl cyclic enones starting from & / #945 / -methyl-& / #946 / -methoxy cyclic enone is described. Manganese (III) acetate-mediated acetoxylation followed by the enzyme-mediated hydrolysis of & / #945 / &rsquo / -acetoxy enone provides acetoxy enones. The reduction of the hydroxy enone, obtained from hydrolysis, furnished both enantiomers of 4-hydroxy enone or & / #947 / -hydroxy enone by using LiAlH4. This study is a model for the synthesis of these type compounds
| Identifer | oai:union.ndltd.org:METU/oai:etd.lib.metu.edu.tr:http://etd.lib.metu.edu.tr/upload/1252519/index.pdf |
| Date | 01 January 2004 |
| Creators | Kose, Elif |
| 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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