Development of Novel Nucleophile-Intercepted Beckmann Fragmentations and Progress Toward the Total Synthesis of 2(S)-Cathafoline
Date of Award
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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.
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.