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The Development of Ni-Catalyzed Methods for Application in Total Synthesis


Shimozono, Alexander Mitsuo (2023) The Development of Ni-Catalyzed Methods for Application in Total Synthesis. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/h0w0-1d25.


The total synthesis of complex natural products often requires the development of mild, selective transformations. Once developed, these methods can serve as starting points for related methodologies, fundamental mechanistic studies, or applied in other total syntheses. Herein, a series of projects that embody this relationship are described. Inspired by unexpected challenges in the synthesis of complex diterpenoid alkaloid talatisamine, a Ni-catalyzed enol-triflate-halogen exchange reaction was developed. In addition to finding application toward the synthesis of talatisamine, this reaction found further use in an attempted route toward enmein-type ent-kauranoid natural products. En route to the synthesis of these natural products, a need for meso-anhydride functionalization was identified which inspired a research program dedicated to Ni-catalyzed reductive functionalization of anhydrides.

Item Type:Thesis (Dissertation (Ph.D.))
Subject Keywords:Ni catalysis, total synthesis
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Public (worldwide access)
Research Advisor(s):
  • Reisman, Sarah E.
Thesis Committee:
  • Stoltz, Brian M. (chair)
  • Agapie, Theodor
  • Robb, Maxwell J.
  • Reisman, Sarah E.
Defense Date:25 October 2022
Non-Caltech Author Email:alex.shimozono (AT)
Funding AgencyGrant Number
NSF Center for Synthetic Organic ElectrochemistryCHE-2002158
Record Number:CaltechTHESIS:11032022-004822338
Persistent URL:
Related URLs:
URLURL TypeDescription relevant to Ch. 1
Shimozono, Alexander Mitsuo0000-0001-7164-4741
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:15055
Deposited By: Alexander Shimozono
Deposited On:21 Dec 2022 16:17
Last Modified:08 Nov 2023 00:42

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[img] PDF (Intro and TOC) - Final Version
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[img] PDF (Chapter 1) - Final Version
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[img] PDF (Appendix 1) - Final Version
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[img] PDF (About the Author) - Final Version
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