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    • University of Missouri-Columbia
    • Graduate School - MU Theses and Dissertations (MU)
    • Theses and Dissertations (MU)
    • Dissertations (MU)
    • 2007 Dissertations (MU)
    • 2007 MU dissertations - Freely available online
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    Diels-alder reactions of a cyclopentadienone derivative

    Gomes, Maria Goretti, 1971-
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    Date
    2007
    Format
    Thesis
    Metadata
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    Abstract
    An ester derivative of cyclopentadienone, a very reactive species, was generated from methyl-2-bromo-3-oxocyclopent-1-enecarboxylate (96) which dimerized instantaneously and decarbonylated to generate an indanone (97). Diels-Alder reactions were performed by trapping this fleeting cyclopentadienone derivative with electron rich dienes to generate [4+2] Diels-Alder adducts. The cycloadducts were diastereo- and regioselective. The yields of these reactions were moderate to high. A wide range of dienes were used to show the versatility and scope of these reactions. Using the developed methodology, at attempt was taken to synthesize steroidal drug desogestrel (218).
    URI
    https://doi.org/10.32469/10355/4670
    https://hdl.handle.net/10355/4670
    Degree
    Ph. D.
    Thesis Department
    Chemistry (MU)
    Rights
    OpenAccess.
    This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivs 3.0 License.
    Collections
    • 2007 MU dissertations - Freely available online
    • Chemistry electronic theses and dissertations (MU)

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