Two enantiodivergent syntheses of balanol and the chemoenzymatic synthesis of oseltamivir
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 |
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 |
refterms.dateFOA | 2021-07-16T11:52:38Z |