Date of Award

Fall 12-15-2022

Document Type

Thesis (Master's)

Department or Program


First Advisor

Jimmy Wu


This thesis is comprised of two chapters, the first being the discovery of a novel nucleophile-intercepted Beckmann fragmentation of [2.2.1] indoline systems that resulted in highly stereo- and regioselective reactions. Chapter one details the exploration of this reaction as well as its relevant background information detailing its significance. Chapter two describes the application of the novel nucleophile-intercepted Beckmann fragmentation in the context of a total synthesis of akuammilline alkaloid 2(S)-cathafoline. While the target natural product was never synthesized, unpredicted reactivity resulted in interesting discoveries worthy of discussion.