Towards the total synthesis of novenamine and its analogues with modifications at C-4 and C-5

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.

Grantor dc:publisher.institution

Department of Chemistry

Year dc:date.issued

2004

Author dc:creator

• Wilson, Seanette Ann

Advisors dc:contributor.advisor

• Hunter, Roger
• Gammon, David W

Language dc:language.iso

eng

Handle dc:identifier.uri

http://hdl.handle.net/11427/6282

OAI identifier oai:identifier

oai:open.uct.ac.za:11427/6282