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    Novel (homo-)Nazarov approaches to complex polycycles and application to bioactive targets

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    WILLIAMS-DISSERTATION-2018.pdf (17.27Mb)
    Date
    2018-07-25
    Author
    Williams, Corey Wayne
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    Abstract
    Complex carbocycles and heterocycles make up a large majority of natural product scaffolds and active pharmaceutical ingredient cores. As a result of this, developing methods to obtain such scaffolds in new, greener, and more modular ways remains an invaluable objective within the synthetic organic community. In this thesis, a number of exciting new methodologies have been developed to access some of these scaffolds, and significant progress is shown toward the application of these methodologies to access pharmaceutically-relevant cores: (1) a chemodivergent and catalytic interrupted, formal homo-Nazarov cyclization to access densely functionalized carbocycles, (2) the application of homo-Nazarov methodology toward the anticancer natural product, Propolisbenzofuran B, and (3) the application of Nazarov-like, Friedel- Crafts methodology toward the antimalarial natural product, Flinderole A. These methodological transformations are tolerant of a variety of functionalities, thus giving broad substrate scope. These syntheses seek to have modular key transformations that will allow formation of a wide variety of non-natural analogs, thus providing rapid access to a compound library useful in the study of structure-activity relationships.
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    http://hdl.handle.net/1853/60299
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    • Georgia Tech Theses and Dissertations [23877]
    • School of Chemistry and Biochemistry Theses and Dissertations [1525]

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