Racemic metyhl 3-cyclohexene-1-carboxylate was resolved via enzymatic hydrolysis to afford the enantiomerically enriched 3-cyclohexene-1-carboxylic acid with PLE (S-configuration), HLE (S-configuration), CCL (S-configuration) and PPL (R-configuration) . The nucleoside& / #65533 / s precursor, 5-(hydroxymethyl)-2-cyclohexen-1-ol (19), was synthesized by iodolactonization, followed by iodine elimination and the reduction of the lactone.
In connection with this work, alpha,beta-unsaturated and saturated cyclic ketones were selectively oxidized on alpha' / - and alpha-positions using Mn(OAc)3 and Pb(OAc)4, respectively. The resultant racemic alpha' / - and alpha-acetoxylated substrates were resolved into corresponding enantiomerically enriched alpha' / - and alpha-hydroxylated and acetoxylated compounds via PLE hydrolysis.
| Identifer | oai:union.ndltd.org:METU/oai:etd.lib.metu.edu.tr:http://etd.lib.metu.edu.tr/upload/12604854/index.pdf |
| Date | 01 April 2004 |
| Creators | Turkut, Engin |
| Contributors | Tanyeli, Cihangir |
| 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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