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dc.contributor.authorSulliva, Braddord Thomas
dc.date.accessioned2010-10-25T19:52:10Z
dc.date.available2010-10-25T19:52:10Z
dc.date.issued2010-10-25
dc.identifier.urihttp://hdl.handle.net/10464/3039
dc.description.abstractThe present thesis outlines our latest findings on the reactivity of the Burgess reagent with oxiranes. Structural, mechanistic, and computational studies are presented. Included is the development of a (-)-menthyl version of the Burgess reagent and its application to the synthesis of enantiomerically pure ~-amino alcohols. This methodology has been exploited in the formal enantiodivergent synthesis of the (+)- and (-)-isomers of balanol. Also described is a second generation approach to both balanol enantiomers; each commencmg with the chemoenzymatic dihydroxylation of bromobenzene. This study also describes the steric and functional limitations of the toluene dioxygenase-mediated oxidation of benzoate esters. The metabolite derived from ethyl benzoate was employed in a formal synthesis of oseltamivir. Finally, several synthetic approaches to oseltamivir and its analogs are presented, each proceeding through a different vinyl aziridine derived from bromobenzene and ethyl benzoate.en_US
dc.language.isoengen_US
dc.publisherBrock Universityen_US
dc.subjectOrganic compounds -- Synthesisen_US
dc.subjectAntiviral agentsen_US
dc.subjectCarbamatesen_US
dc.titleTwo enantiodivergent syntheses of balanol and the chemoenzymatic synthesis of oseltamiviren_US
dc.typeElectronic Thesis or Dissertationen_US
dc.degree.namePh.D. Biotechnologyen_US
dc.degree.levelDoctoralen_US
dc.contributor.departmentCentre for Biotechnologyen_US
dc.degree.disciplineFaculty of Mathematics and Scienceen_US


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