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Synthetic Studies Toward the Total Synthesis of Enterocin


Tao, Yujia (2023) Synthetic Studies Toward the Total Synthesis of Enterocin. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/jdhq-sb66.


As part of a broader program aimed at the synthesis of complex and highly oxygenated natural products, we initiated a chemical synthesis of the natural polyketide enterocin. This dissertation will disclose our efforts to bridge that gap through the development of synthetic strategies for the total synthesis of the enterocin. The studies herein will address three unique strategies to access the tactical difficulties in the rich oxygenation patterns and caged core structure of enterocin. The program was first inspired by a SeO2 multioxidation reaction, and the methodology has been successfully applied to install bridgehead oxygenation patterns in enterocin. A strategy featuring a radical-polar crossover reaction as an annulation step to quickly construct the [3.2.1] bicyclic core of enterocin is detailed. Initial studies have successfully achieved the radical-polar crossover annulation reaction to forge [3.2.1]bicycles with bridgehead hydroxyl groups, and will guide the future development toward the total synthesis of enterocin. An intermolecular aldol approach will be discussed to address the challenge on pyrone installation and core structure synthesis. In summary, the development of an efficient and general approach will allow the development of novel reactions and a comprehensive evaluation of the potential of caged polyketides to serve as medicinally interesting molecules.

Item Type:Thesis (Dissertation (Ph.D.))
Subject Keywords:Total Synthesis, Organic Chemistry
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Not set
Research Advisor(s):
  • Reisman, Sarah E.
Thesis Committee:
  • Stoltz, Brian M. (chair)
  • Arnold, Frances Hamilton
  • Fu, Gregory C.
  • Reisman, Sarah E.
Defense Date:5 May 2023
Non-Caltech Author Email:yjtao8 (AT)
Funding AgencyGrant Number
Record Number:CaltechTHESIS:05182023-054024067
Persistent URL:
Related URLs:
URLURL TypeDescription adapted for ch.1 adapted for ch.2 article published
Tao, Yujia0000-0003-4615-6409
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:15189
Deposited By: Yujia Tao
Deposited On:26 May 2023 22:34
Last Modified:08 Nov 2023 00:42

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