Stereoselective Synthesis of Organoboron Reagents and their Application Toward the Synthesis of Amphidinolides C and F

Abstract

This dissertation details three main projects that focus on stereoselective synthesis of organoboron reagents and their application to total synthesis studies. The first chapter describes the development of an enantioselective palladium-catalyzed conjuntive cross-coupling of bis(alkenyl)borates to access chiral allylboron reagents. These reagents are of high synthetic value that is demonstrated through various applications. The second chapter describes the development of a diastereoselective amine-modified boron-Wittig reaction with ketone electrophiles to access trisubstituted alkenyl boronic esters. The synthetic utility of these trisubstituted alkenyl boronic esters is demonstrated through a novel palladium-catalyzed cross-coupling reaction. The third chapter encompassess studies toward the total synthesis of natural products amphidinolides C and F. It highlights the application of methods developed in the Morken laboratory in the context of challenging total synthesis. It also highlights the potential for newly developed conjunctive cross-coupling and boron-Wittig reactions to solve problems in total synthesis.