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    Novel syntheses of cis and trans isomers of combretastatin A-4.

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    Authors
    Gaukroger, Keira
    Hadfield, John A
    Hepworth, Lucy A
    Lawrence, Nicholas J
    McGown, Alan T
    Affiliation
    CRC Drug Development Group and CRC Radiochemical Targeting and Imaging Group, Paterson Institute for Cancer Research, Christie Hospital NHS Trust, Manchester, M20 4BX, U.K.
    Issue Date
    2001-11-30
    
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    Abstract
    A high-yielding, two-step stereoselective synthesis of the anticancer drug (Z)-combretastatin A-4 (1) has been devised. The method uses the Perkin condensation of 3,4,5-trimethoxyphenylacetic acid and 3-hydroxy-4-methoxybenzaldehyde followed by decarboxylation of the cinnamic acid intermediate using copper and quinoline. The iodine-catalyzed isomerization of the Z isomer 1 results in complete conversion to the E isomer. The Suzuki cross-coupling of an aryl boronic acid and vinyl bromide has also been successfully employed to produce both Z and E isomers of combretastatin A-4 stereoselectively. Both methods are far superior to the current five-step Wittig synthesis in which both isomers are produced nonstereoselectively.
    Citation
    Novel syntheses of cis and trans isomers of combretastatin A-4. 2001, 66 (24):8135-8 J. Org. Chem.
    Journal
    The Journal of Organic Chemistry
    URI
    http://hdl.handle.net/10541/85532
    DOI
    10.1021/jo015959z
    PubMed ID
    11722216
    Type
    Article
    Language
    en
    ISSN
    0022-3263
    ae974a485f413a2113503eed53cd6c53
    10.1021/jo015959z
    Scopus Count
    Collections
    All Paterson Institute for Cancer Research

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