Synthesis of Organic Building Blocks and Synthetic Strategies Toward Aleutianamine

Citation

Sercel, Zachary Patrick (2023) Synthesis of Organic Building Blocks and Synthetic Strategies Toward Aleutianamine. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/3ezw-2h57. https://resolver.caltech.edu/CaltechTHESIS:05312023-053933898

Abstract

Described herein are the development of the palladium-catalyzed decarboxylative asymmetric allylic alkylation of medicinally relevant 5- and 7-membered diazaheterocycles and efforts toward the total synthesis of the cytotoxic pyrroloiminoquinone marine alkaloid aleutianamine. The former methodology provides a new tactic to incorporate Csp3 structural complexity into future lead compounds containing diazepane and imidazolidine moieties. The latter project is ongoing.

Additionally, Chapter 3 discusses preliminary attempts to improve the synthetic accessibility of minimally substituted corroles, which were conducted during a research internship in the laboratory of Prof. Zeev Gross at the Technion. During the course of this research, the first example of a β-unsubstituted free base monoazaporphyrin was isolated, and its cobalt complex was characterized by x-ray crystallography.

Finally, Appendix 8 presents a series of cationic and radical-mediated fragmentations of a derivative of (+)-3-Carene, a chiral pool material. These experiments led to the observation and mechanistic study of an unexpected rearrangement.

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