Leveraging C-X Bonds for Triggered Eliminations, Alkene Functionalizations, and Intramolecular Cyclizations

Chemists continue to take inspiration from nature when it comes to finding and creating biologically relevant compounds. Two branches of organic synthesis—methodological development and target-oriented syntheses—serve different functions towards the same goal in medicinally chemistry. Probing new chemical space by way of developing novel synthetic methods to heterocyclic compounds is one of two foci of this work. In partnership with Pfizer Inc, development of alkoxyazomethine ylide cycloaddition methods were explored and investigated in attempt to access complex pyrrolidine compounds of purely synthetic design. The second foci of this work sought to leverage known natural chemical processes and adapt them for synthetic replication. Marine sources of natural products continue to produce exceptionally unique compound scaffolds, with demonstrated activities against a wide array of microorganisms. One such class of compounds is the macrolide compound family isolated for the macroalgae Callophycus serratus. With no current total syntheses completed to-date however, there is no efficient way to access these compounds in a cost-effective manner. To aid in this venture, novel methods were developed to key structural components of these macrolide compounds, in addition to other synthetic-focused methodology and reaction discovery.Ph.D