Date of Completion
5-29-2015
Embargo Period
5-27-2016
Major Advisor
Dr. Mark W. Peczuh
Associate Advisor
Dr. Michael B. Smith
Associate Advisor
Dr. William F. Bailey
Field of Study
Chemistry
Degree
Doctor of Philosophy
Open Access
Campus Access
Abstract
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.
Recommended Citation
Lorenc, Chris, "Methods Development and New Reaction Discovery in the Synthesis of Natural Product-like Molecules" (2015). Doctoral Dissertations. 840.
https://digitalcommons.lib.uconn.edu/dissertations/840