Complexity-Building Transformations of Silyl Glyoxylates Public Deposited

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Last Modified
  • March 20, 2019
Creator
  • Schmitt, Daniel Copley
    • Affiliation: College of Arts and Sciences, Department of Chemistry
Abstract
  • Silyl glyoxylates are reagents used for the geminal difunctionalization of a glycolic acid junction with nucleophilic and electrophilic species. The research summarized herein describes the development of new reactions that utilize silyl glyoxylates to generate multiple C-C bonds and stereogenic centers. Significant results include: (1) completion of the synthesis of (+)-zaragozic acid C; (2) development of a tandem Brook/Ireland Claisen rearrangement for the synthesis of functionalized a,b-unsaturated glycolic acids; (3) development of a nitrile-oxide cycloaddition for the synthesis of 3,4-disubstituted isoxazoles; (4) development of a three component glycolate Michael reaction; (5) application of the glycolate Michael reaction to the synthesis of (+)-trachyspic acid dimethyl ester.
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  • In Copyright
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  • "... in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the Department of Chemistry."
Advisor
  • Johnson, Jeffrey
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Place of publication
  • Chapel Hill, NC
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  • Open access
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