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    Part I. Approaches Toward the Total Synthesis of Tyloindicine F; Part II. Palladium-Catalyzed C−H Functionalization of β-enaminones

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    Issue Date
    2010-02-26
    Author
    Bi, Lei
    Publisher
    University of Kansas
    Format
    175 pages
    Type
    Dissertation
    Degree Level
    Ph.D.
    Discipline
    Medicinal Chemistry
    Rights
    This item is protected by copyright and unless otherwise specified the copyright of this thesis/dissertation is held by the author.
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    Abstract
    Tyloindicine F is a potent anticancer natural product first isolated from the Himalaya region of India. It demonstrated a unique profile in the NCI60 human tumor cell line anticancer drug screen. Due to its scarcity from natural sources, a total synthesis of tyloindicine F is desirable. Two attempts at the synthesis of this natural product have been conducted and are discussed. β-enaminones are a group of push-pull olefins whereas C-H functionalization/C-C coupling is a highly efficient method of constructing new carbon-carbon bonds. β-enaminones are highly polarized and their β; position is suitable for C-H functionalization by means of electropalladation. A novel methodology for the oxidative Hiyama coupling of β-enaminones has been developed and two new bifunctional activators/reoxidants have been found. Furthermore, a non-oxidative version for β-enaminone C-H functionalization and the decarboxylative coupling of β-enaminones were also investigated.
    URI
    http://hdl.handle.net/1808/6280
    Collections
    • Dissertations [4473]
    • Medicinal Chemistry Dissertations and Theses [81]

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    785-864-8983
    KU Libraries
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    785-864-8983

    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
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    Contact KU ScholarWorks
    785-864-8983
    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    785-864-8983

    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    Image Credits
     

     

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