(2S)-trans-4-Hydroxyproline has been studied as a chiral template for the preparation of kainoids. Conversion to protected 4-ketoproline derivatives has allowed functionalisation at C-3 to be investigated. Although the tendency to epimerisation has caused problems, we have successfully introduced a variety of alkyl side chains with cis stereochemistry at this position. Functionalisation of the 3-alkyl-4-ketoprolines at C-4 has been investigated and a method has been found to prepare compounds which are functionalised stereospecifically at both C-3 and C-4. These have potential for study as kainate analogues. During our studies on the synthesis of kainoids, an unusually stereospecific deuteriation has been discovered. We have exploited this in a synthesis of (2S,3S)-[3- 2Ht]-proline, (2S,3R)-[3-2Ht]-proline and (2S)-[3,3-2H21-proline.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:239542 |
| Date | January 1994 |
| Creators | Spray, Caroline Ann |
| Publisher | University of Sussex |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
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