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Two enantiodivergent syntheses of balanol and the chemoenzymatic synthesis of oseltamivir

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dc.contributor.author Sulliva, Braddord Thomas
dc.date.accessioned 2010-10-25T19:52:10Z
dc.date.available 2010-10-25T19:52:10Z
dc.date.issued 2010-10-25
dc.identifier.uri http://hdl.handle.net/10464/3039
dc.description.abstract The 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.iso eng en_US
dc.publisher Brock University en_US
dc.subject Organic compounds -- Synthesis en_US
dc.subject Antiviral agents en_US
dc.subject Carbamates en_US
dc.title Two enantiodivergent syntheses of balanol and the chemoenzymatic synthesis of oseltamivir en_US
dc.type Electronic Thesis or Dissertation en_US
dc.degree.name Ph.D. Biotechnology en_US
dc.degree.level Doctoral en_US
dc.contributor.department Centre for Biotechnology en_US
dc.degree.discipline Faculty of Mathematics and Science en_US


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