ABSTRACT
STEREOSELECTIVE SYNTHESIS OF OPTICALLY ACTIVE CYCLITOL
PRECURSORS VIA CHEMOENZYMATIC METHOD
AND
SYNTHESIS OF A NUCLEOSIDE PRECURSOR
Oguzkaya, Funda
M.S., Department of Chemistry
Supervisor: Prof. Dr. Cihangir Tanyeli
June 2006, 99 pages
& / #945 / ' / -acetoxylation of & / #945 / ,ß / -unsaturated cyclic ketones was adjusted via Mn(OAc)3 in regioselective manner. Then, PLE hydrolysis was carried out so as to afford enantiomerically enriched & / #945 / ' / -acetoxylated and & / #945 / ' / -hydroxylated cyclic compounds. From our knowledge about the literature and previous works dealing with & / #945 / ' / -hydroxylated products which are easily racemized, protection was directly adjusted via acetylation so as to prevent this possibility. Resulting enantiomerically enriched products were subjected to Upjohn Dihydroxylation to obtain cyclitol precursors and following Luche Reduction of ketone was adjusted so as to obtain corresponding cyclitols.
In addition with such synthetic design, firstly dimethyl cyclopent-3-ene-1,1-dicarboxylate was obtained so as to reach in former manner 3-cyclopentene-1,1-dicarboxylic acid, and in latter manner cyclopent-3-enecarboxylic acid. Resulting compound was converted to 6-iodo-2-oxa-bicyclo[2.2.1]heptan-3-one and followingly to the target nucleoside precursor which is 2-oxa-bicyclo[2.2.1]hept-5-en-3-one.
| Identifer | oai:union.ndltd.org:METU/oai:etd.lib.metu.edu.tr:http://etd.lib.metu.edu.tr/upload/2/12607324/index.pdf |
| Date | 01 June 2006 |
| Creators | Oguzkaya, Funda |
| 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 METU campus |
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