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  • The Stereocontrolled Total Synthesis of Altohyrtin A/Spongistatin 1: The Southern Hemisphere EF Segment

    Author(s)
    Paterson, I
    Coster, MJ
    Chen, DYK
    Acena, JL
    Bach, J
    Keown, LE
    Trieselmann, T
    Griffith University Author(s)
    Coster, Mark J.
    Year published
    2005
    Metadata
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    Abstract
    The fully functionalised C29-C51 southern hemisphere of altohyrtin A/spongistatin 1 (1), incorporating the E- and F-ring tetrahydropyran rings and the unsaturated side chain, has been synthesised in a highly convergent and stereocontrolled manner. Key steps in the synthesis of this phosphonium salt include four highly diastereoselective, substrate-controlled, boron aldol reactions to establish key C-C bonds and accompanying stereocentres, where the introduction of the chlorodiene side chain and the C47 hydroxyl-bearing centre were realised by exploiting remote stereoinduction from the F-ring tetrahydropyran.The fully functionalised C29-C51 southern hemisphere of altohyrtin A/spongistatin 1 (1), incorporating the E- and F-ring tetrahydropyran rings and the unsaturated side chain, has been synthesised in a highly convergent and stereocontrolled manner. Key steps in the synthesis of this phosphonium salt include four highly diastereoselective, substrate-controlled, boron aldol reactions to establish key C-C bonds and accompanying stereocentres, where the introduction of the chlorodiene side chain and the C47 hydroxyl-bearing centre were realised by exploiting remote stereoinduction from the F-ring tetrahydropyran.
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    Journal Title
    Organic & Biomolecular Chemistry
    Volume
    3
    DOI
    https://doi.org/10.1039/b504149j
    Subject
    Medicinal and biomolecular chemistry
    Organic chemistry
    Publication URI
    http://hdl.handle.net/10072/22609
    Collection
    • Journal articles

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