Date of Completion


Embargo Period


Major Advisor

Dr. Mark W. Peczuh

Associate Advisor

Dr. Michael B. Smith

Associate Advisor

Dr. William F. Bailey

Field of Study



Doctor of Philosophy

Open Access

Campus Access


Modern synthetic methods aim at high efficiency in terms of atom economy and yield while at the same time minimizing the number of synthetic steps and purification processes. Identification and development of new reactions plays an important role in the advancement of synthetic organic chemistry. The reactions enable the preparation of previously inaccessible compounds or they may streamline a synthetic sequence of a known compound. Chemists have been and continue to improve on the current methods reported in the literature through thoughtful consideration of reaction mechanisms and practical parameters. Serendipity, however, also plays a role in developing methods as has been noted many times that one discovers something else than what one was looking for, as was with the discovery of penicillin. This dissertation reports on three areas of methods development and reaction discovery: 1 – a new method for the synthesis of glycosylated small molecule libraries using desosamine as a model system, 2 - a rapid route to a new class of polycyclic spiroketals via an isomerization-dimerization pathway and the novel rearrangement of the products via oxidation, and 3 – the development and application of a carbamoyl anion addition reaction.