Towards the total synthesis of novenamine and its analogues with modifications at C-4 and C-5
Doctoral Thesis
2004
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University of Cape Town
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Abstract
Novenamine, a known antibacterial agent, is composed of 3-0-carbamoyl noviose (novobiose) glycosidically linked to a 4-hydroxy-3-amino-coumarin unit. Its activity as a DNA-gyrase inhibitor and the absence of analogues containing 4-epi-noviose provided the rationale for developing new synthetic routes to these analogues. This thesis describes the total synthesis of the methyl glycosides of noviose and C-4-epi-noviose, methodology for the introduction of the C-3 carbamoyl group to both isomers, an alternative synthesis of the coumarin component, progress towards a C-5 analogue of 4-epi-noviose and a model study of methodology for the glycosidic coupling of the coumarin unit to suitably activated sugars.
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Includes bibliographical references.
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Wilson, S. 2004. Towards the total synthesis of novenamine and its analogues with modifications at C-4 and C-5. University of Cape Town.