A Caltech Library Service

Synthesis of Organic Building Blocks and Synthetic Strategies Toward Aleutianamine


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.


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.

Item Type:Thesis (Dissertation (Ph.D.))
Subject Keywords:chemistry, organic, synthesis, palladium, allylic alkylation, synthetic methods, natural products
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Stoltz, Brian M.
Thesis Committee:
  • Robb, Maxwell J. (chair)
  • Gray, Harry B.
  • Reisman, Sarah E.
  • Stoltz, Brian M.
Defense Date:24 May 2023
Funding AgencyGrant Number
NSF Graduate Research FellowshipDGE-1745301
Record Number:CaltechTHESIS:05312023-053933898
Persistent URL:
Related URLs:
URLURL TypeDescription DocumentArticle Adapted for Chapter 1 DocumentArticle Adapted for Chapter 1 DocumentArticle Adapted for Appendix 8
Sercel, Zachary Patrick0000-0001-7977-8509
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:15242
Deposited By: Zachary Sercel
Deposited On:02 Jun 2023 15:28
Last Modified:06 Dec 2023 19:46

Thesis Files

[img] PDF (Final Version) - Final Version
See Usage Policy.


Repository Staff Only: item control page