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Title: 4-ketoproline derivatives as chiral templates in synthesis.
Author: Spray, Caroline Ann.
ISNI:       0000 0001 3475 5979
Awarding Body: University of Sussex
Current Institution: University of Sussex
Date of Award: 1994
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(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.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Kainic acid; Amino acids