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.
