| 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 beta-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 commencing 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 bromobenzeneand ethyl benzoate. |
