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

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dc.contributor.advisorHunter, Rogeren_ZA
dc.contributor.advisorGammon, David Wen_ZA
dc.contributor.authorWilson, Seanette Annen_ZA
dc.date.accessioned2014-08-13T14:25:29Z
dc.date.available2014-08-13T14:25:29Z
dc.date.issued2004en_ZA
dc.descriptionIncludes bibliographical references.en_ZA
dc.description.abstractNovenamine, 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.en_ZA
dc.identifier.apacitationWilson, S. A. (2004). <i>Towards the total synthesis of novenamine and its analogues with modifications at C-4 and C-5</i>. (Thesis). University of Cape Town ,Faculty of Science ,Department of Chemistry. Retrieved from http://hdl.handle.net/11427/6282en_ZA
dc.identifier.chicagocitationWilson, Seanette Ann. <i>"Towards the total synthesis of novenamine and its analogues with modifications at C-4 and C-5."</i> Thesis., University of Cape Town ,Faculty of Science ,Department of Chemistry, 2004. http://hdl.handle.net/11427/6282en_ZA
dc.identifier.citationWilson, S. 2004. Towards the total synthesis of novenamine and its analogues with modifications at C-4 and C-5. University of Cape Town.en_ZA
dc.identifier.ris TY - Thesis / Dissertation AU - Wilson, Seanette Ann AB - 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. DA - 2004 DB - OpenUCT DP - University of Cape Town LK - https://open.uct.ac.za PB - University of Cape Town PY - 2004 T1 - Towards the total synthesis of novenamine and its analogues with modifications at C-4 and C-5 TI - Towards the total synthesis of novenamine and its analogues with modifications at C-4 and C-5 UR - http://hdl.handle.net/11427/6282 ER - en_ZA
dc.identifier.urihttp://hdl.handle.net/11427/6282
dc.identifier.vancouvercitationWilson SA. Towards the total synthesis of novenamine and its analogues with modifications at C-4 and C-5. [Thesis]. University of Cape Town ,Faculty of Science ,Department of Chemistry, 2004 [cited yyyy month dd]. Available from: http://hdl.handle.net/11427/6282en_ZA
dc.language.isoengen_ZA
dc.publisher.departmentDepartment of Chemistryen_ZA
dc.publisher.facultyFaculty of Scienceen_ZA
dc.publisher.institutionUniversity of Cape Town
dc.subject.otherChemistryen_ZA
dc.titleTowards the total synthesis of novenamine and its analogues with modifications at C-4 and C-5en_ZA
dc.typeDoctoral Thesis
dc.type.qualificationlevelDoctoral
dc.type.qualificationnamePhDen_ZA
uct.type.filetypeText
uct.type.filetypeImage
uct.type.publicationResearchen_ZA
uct.type.resourceThesisen_ZA
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