Date of Award
Fall 12-15-2022
Document Type
Thesis (Master's)
Department or Program
Chemistry
First Advisor
Jimmy Wu
Abstract
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.
Recommended Citation
Dunkley, Evan M., "Development of Novel Nucleophile-Intercepted Beckmann Fragmentations and Progress Toward the Total Synthesis of 2(S)-Cathafoline" (2022). Dartmouth College Master’s Theses. 66.
https://digitalcommons.dartmouth.edu/masters_theses/66