INVESTIGATIONS TOWARD THE APPLICATION OF ORGANIC PHOTOREDOX CATALYSIS TO THE SYNTHESIS OF NATURAL PRODUCTS

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  • Roth, Hudson Gordon
    • Affiliation: College of Arts and Sciences, Department of Chemistry
Abstract
  • While chemistry proceeding through radical intermediates has been known and studied for centuries, photoredox catalysis as a means of generating these species has only entered the forefront of synthetic organic chemistry within the past few decades. This approach has gained traction due to the use of visible light and generally mild conditions, making it compatible with a range of functional groups and late-stage functionalization. Chapters 1 and 2 of this work focus on photoredox catalysis in general. The first chapter covers the basic principles of photoredox catalysis, giving special attention to acridinium ion dyes as photoredox catalysts; in addition, select applications of acridinium ion photoredox catalysis to the synthesis of natural products are discussed. The second chapter details the importance of electrochemical potentials in planning and conducting photoredox transformations. Our work on compiling a database of experimental and computational potentials, and a collaboration with Merck on the advantages of organic photoredox catalysis are presented. Chapters 3 and 4 focus on our endeavors to apply acridinium ion photoredox catalysis to the synthesis of the natural products rubriflordilactone B and stemocurtisine. This work has culminated in a diastereoselective route to the left side of rubriflordilactone B and preliminary results for an approach to stemocurtisine.
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Advisor
  • Nicewicz, David A
  • Wilkerson-Hill, Sidney M
  • Knight, Abigail S
  • Leibfarth, Frank A
  • You, Wei
Degree
  • Doctor of Philosophy
Degree granting institution
  • University of North Carolina at Chapel Hill Graduate School
Graduation year
  • 2020
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