UCLA

The first chapter of this thesis outlines my progress towards establishing the first total synthesis of the natural product JBIR-141. The preliminary sections cover relevant literature on the natural product including work done by others. Further sections detail the retrosynthetic analysis of the natural product alongside the synthesis of several fragments and their designs. These sections outline the synthetic approach to the natural product which emphasizes convergency and modularity. Further detailed is our plan towards completion of the route as well as plans to identify the compound’s active pharmacophore to elucidate its mechanism of action and maximize its potential as a chemotherapeutic agent. The second chapter covers my work on octafluorocyclopentene (OFCP) derived peptidyl macrobicycles and our attempt to identify structural motifs that increase their passive permeability as measured by Parallel Artificial Membrane Permeability Assay (PAMPA) kit.