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Development of a Synthetic Strategy Toward Falcatin A. Development of an Asymmetric Diels–Alder Reaction of α-Acyloxy Enones

Citation

Mendoza, Skyler Dakota (2022) Development of a Synthetic Strategy Toward Falcatin A. Development of an Asymmetric Diels–Alder Reaction of α-Acyloxy Enones. Dissertation (Ph.D.), California Institute of Technology. doi:10.7907/v3ys-kj69. https://resolver.caltech.edu/CaltechTHESIS:11062021-003540914

Abstract

Accessing natural products via de novo synthetic methods is important for the discovery of new medicines, antibiotics, agrochemicals, and more. Design and investigation of efficient strategies is of interest to many pharmaceutical industries.

Herein, we discuss several strategies geared towards the synthesis of the natural product falcatin A. First, a general discussion of the class of natural products is discussed. Secondly, we discuss our first generation photoredox cascade cyclization approach toward the synthesis of falcatin A. This strategy allows for the efficient and convergent synthesis of two halves of falcatin. Next, a transition metal-catalyzed cascade cyclization approach is discussed in which we were able to successfully synthesize the core of the natural product on a model system. Efforts are ongoing to elaborate to more advanced fragments for the synthesis of falcatin A. Lasty, we discuss our work on the yttrium-catalyzed asymmetric Diels–Alder reaction of α-acyloxy enone dienophiles, performed in collaboration with BASF. We demonstrate that this methodology can be utilized to access enantioenriched natural product T-4-ol.

Item Type:Thesis (Dissertation (Ph.D.))
Subject Keywords:Synthesis, Organic
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Thesis Availability:Restricted to Caltech community only
Research Advisor(s):
  • Reisman, Sarah E.
Group:Reisman Group
Thesis Committee:
  • Fu, Gregory C. (chair)
  • Stoltz, Brian M.
  • Peters, Jonas C.
  • Reisman, Sarah E.
Defense Date:25 October 2021
Record Number:CaltechTHESIS:11062021-003540914
Persistent URL:https://resolver.caltech.edu/CaltechTHESIS:11062021-003540914
DOI:10.7907/v3ys-kj69
ORCID:
AuthorORCID
Mendoza, Skyler Dakota0000-0003-1939-1884
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:14419
Collection:CaltechTHESIS
Deposited By: Skyler Mendoza
Deposited On:12 Nov 2021 20:39
Last Modified:13 Jul 2022 22:48

Thesis Files

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