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The Modular Synthesis and Functionalization of Cyclic Compounds Using Modern Methods


Lacker, Caitlin Rebecca (2022) The Modular Synthesis and Functionalization of Cyclic Compounds Using Modern Methods. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/61ky-5w83.


Accessing libraries of similar compounds quickly is important in the pharmaceutical industry, as it allows for the expedient investigation of a wide variety of parameters. An efficient strategy to access compounds of interest is to start from a single intermediate containing an interesting or pharmaceutically active structure and decorating it with varying functionality to generate a library of related compounds. Cross-coupling is a powerful tool for this type of divergent, modular approach.

Herein, we discuss several strategies geared towards the synthesis of small libraries of compounds of interest. First, a modular approach towards a library of enantioenriched trans cyclobutanes is discussed. This strategy allows for the synthesis of diverse substrates from a single enantioenriched intermediate, and this approach was applied to the synthesis of the small molecule (+)-rumphellaone A. Finally, the development of an enantioselective nickel-catalyzed photoredox cross-coupling to form N-(hetero)benzylic azoles in collaboration with researchers at Merck is discussed.

Item Type:Thesis (Dissertation (Ph.D.))
Subject Keywords:Rumphellaone A, Synthesis, methodology, Wolff Rearrangement, photoredox, cross-coupling, enantioselective
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:
  • Fu, Gregory C. (chair)
  • Reisman, Sarah E.
  • Hsieh-Wilson, Linda C.
  • Stoltz, Brian M.
Defense Date:16 August 2021
Funding AgencyGrant Number
National Science Foundation Graduate Research FellowshipDGE-1144469
Cottrell Fred Award26688
Record Number:CaltechTHESIS:09072021-162545226
Persistent URL:
Related URLs:
URLURL TypeDescription adapted for Chapter 1. adapted for Chapters 1 and 2.
Lacker, Caitlin Rebecca0000-0003-2531-2636
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:14355
Deposited By: Caitlin Lacker
Deposited On:28 Sep 2021 15:57
Last Modified:08 Nov 2023 00:42

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