Two enantiodivergent syntheses of balanol and the chemoenzymatic synthesis of oseltamivir

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.

Name thesis:degree_name

Ph.D. Biotechnology

Level thesis:degree_level

Doctoral

Discipline thesis:degree_discipline

Faculty of Mathematics and Science

Department dc:contributor.department

Centre for Biotechnology

Grantor

Brock University

Year dc:date.issued

2010

Author dc:creator

• Sulliva, Braddord Thomas

• Organic compounds -- Synthesis
• Antiviral agents
• Carbamates

Language dc:language.iso

eng

Handle dc:identifier.uri

http://hdl.handle.net/10464/3039

OAI identifier oai:identifier

oai:brocku.scholaris.ca:10464/3039