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Title: The synthesis of compounds related to naturally occurring flavanoids
Author: Munro, D. N.
Awarding Body: University of Oxford
Current Institution: University of Oxford
Date of Award: 1965
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Flavanoid compounds exist in many parts of plant life and assume various roles which are not yet fully understood. A study of flavanoids based on the flavan-3-ol (I : R=OH, R′=H) and the flavan-3:4-diol (I : R=R′=OH) skeleton, is essential for investigation of the functions fulfilled by flavanoids in plants. The synthesis of such flavanoids of particular stereochemistry requires the development of stereospecific methods. Until recently, confusion existed in the knowledge of the stereochemistry of the heterocyclic ring in flavanoids, and particularly the configurations and conformations existing in flavan-4-ols (I : R=H, R′=OH). A number of simple flavan-4-ols have been synthesised, and their benzoates shown, by a strict examination by nuclear magnetic resonance spectroscopy, to exist in a "half chair" conformation, with the oxygen function axial in the α-flavanols and equatorial in the β-flavanols. Accurate data and interpretation in the α-series has not previously been available; the results for compounds in the β-series are in excellent agreement with those found by other workers.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available