& / #945 / ,& / #946 / -Unsaturated cyclic ketones were selectively oxidized on & / #945 / ' / - positions using Mn(OAc)3 and Pb(OAc)4, respectively. The resultant racemic & / #945 / ' / -acetoxylated substrates were resolved into corresponding enantiomerically enriched & / #945 / ' / -hydroxylated and & / #945 / ' / -acetoxylated compounds via PLE hydrolysis. & / #945 / ' / -Hydroxylated compounds are racemized quickly, so they were acetylated with acetyl chloride and pyridine in situ to give the corresponding & / #945 / ' / -acetoxylated compounds. Resultant & / #945 / ' / -acetoxy & / #945 / ,& / #946 / -unsaturated cyclic ketones reacted with excess amount of diazomethane under the catalsts of Pd(OAc)2 to give the resulting bicyclic diastereomeric products. At the end of the experiment, Enantiomeically enriched 2-oxobicyclo[3.1.0]hexan-3-yl acetate and 2-oxobicyclo[4.1.0]heptan-3-yl acetate were chemoenzymatically synthesized.
| Identifer | oai:union.ndltd.org:METU/oai:etd.lib.metu.edu.tr:http://etd.lib.metu.edu.tr/upload/12606176/index.pdf |
| Date | 01 June 2005 |
| Creators | Atli, Selin |
| 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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