Synthesis of C2 Symmetric Cyclobutanes and gamma-Butyrolactones via Photoinduced Electron Transfer Public Deposited

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  • March 20, 2019
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  • Riener, Michelle
    • Affiliation: College of Arts and Sciences, Department of Chemistry
Abstract
  • Organic Photoredox Catalysis An overview of the principles of photoredox catalysis, alkene oxidation, and discussion of organic and inorganic photooxidants, applied in organic chemistry is discussed. [2+2] Cycloaddition Reactions of Alkenes via Single Electron Transfer Catalysis A novel method for the diastereoselective synthesis of lignan cyclobutanes via dimerization of simple olefins is presented. A unique strategy for controlling detrimental cycloreversion and polymerization processes via the use of appropriately tuned electron relays was developed. This method was applied to the direct synthesis of two naturally produced cyclobutane compounds; Magnosalin, and Pellucidin A, as well as a third natural product, Endiandrin A via derivatization. Synthesis of gamma-Butyrolactones via Polar Radical Crossover Cyclization Reactions of Unsaturated Acids And Alkenes The development of a convergent synthesis of biologically relevant gamma-butyrolactone scaffolds by an electron-transfer mediated polar-radical crossover cycloaddition was covered. This transformation proceeded with exquisite regioselectivity, and relied on the implementation of a dual-catalyst system. The utility of this method was showcased via the synthesis of two bioactive natural products within the paraconic acid family.
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  • In Copyright
Advisor
  • Nicewicz, David
Degree
  • Doctor of Philosophy
Graduation year
  • 2014
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