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    • University of Missouri-Columbia
    • Graduate School - Theses and Dissertations (MU)
    • Theses and Dissertations (MU)
    • Dissertations (MU)
    • 2011 Dissertations (MU)
    • 2011 MU dissertations - Freely available online
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    Formal total synthesis of pseudopteroxale. Progress toward total synthesis of hamigeran B

    Cai, Zhengxin
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    Date
    2011
    Format
    Thesis
    Metadata
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    Abstract
    In the first chapter, a formal total synthesis of pseudopteroxazole is presented, highlightening an E-selective Horner-Emmons reaction, a Buchwald-Hartwig coupling, and a diastereoselective intramolecular Michael addition. In the second chapter, the effort toward synthesizing anti-viral natural product hamigeran B is summarized. Several routes to the core structure were shown separately, including those unexpected discoveries when pursuing those routes. Tius-Nazarov cyclization was first applied in synthesizing natural product; an efficient palladiumcatalyzed oxidative intramolecular carbocyclization was realized on an α-hydroxy enone for the first time; an interrupted Nazarov cyclization of a hydrolysis intermediate of dithiane was achieved.
    URI
    https://hdl.handle.net/10355/14284
    https://doi.org/10.32469/10355/14284
    Degree
    Ph. D.
    Thesis Department
    Chemistry (MU)
    Collections
    • 2011 MU dissertations - Freely available online
    • Chemistry electronic theses and dissertations (MU)

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