University of Minnesota Ph.D. dissertation. August 2018. Major: Medicinal Chemistry. Advisor: Courtney Aldrich. 1 computer file (PDF); xxi, 641 pages.Selectivity in both organic and medicinal chemistries represents the pinnacle of these scientific fields. The ability to do exactly as one intends in the most efficient manner facilitates a limited negative impact technology may impart in the environments in which it acts. As such, during these dissertation studies, I have endeavored to design new selective reactions to enable the most streamlined synthesis of organic molecules that may impart a variety of functions while simultaneously working to rationally create new drug substances that limit side effects in the patient, while also protecting the molecule from the harsh environment of an organism. To briefly summarize the material contained herein, the first chapter comprises of the technologies I have developed for better enabled organic synthesis. These reactions can improve green chemistry initiatives to limit the negative impact on the environment, only possible because of the highly selective nature of these reactions. I expect these technologies should enable chemists who design molecules with many intended purposes, although they were designed with the intent of empowering medicinal chemists. The second chapter of this work covers highly collaborative efforts to design improved chemotherapeutics in an effort to eradicate Tuberculosis, the leading cause of infectious disease mortality worldwide. These molecules range from selective pro-drugs that are released at the site of action by utilizing a selective targeting pro-moiety to rationally designed agents to take advantage of biological mechanism knowledge. These molecules can potentially be drugs in themselves while they certainly inform future endeavors to make new drug materials to combat Tuberculosis
