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  • The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: the CD-spiroacetal segment

    Author(s)
    Paterson, Ian
    Coster, Mark J.
    Chen, David Y.-K.
    Gibson, Karl R.
    Wallace, Debra J.
    Griffith University Author(s)
    Coster, Mark J.
    Year published
    2005
    Metadata
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    Abstract
    Stereocontrolled syntheses of the C16-C28 CD-spiroacetal subunit of altohyrtin A/spongistatin 1 (1), relying on kinetic and thermodynamic control of the spiroacetal formation, are described. The kinetic control approach resulted in a slight preference (60:40) for the desired spiroacetal isomer. The thermodynamic approach allowed ready access to the desired spiroacetal 2 by acid promoted equilibration, chromatographic separation of the C23 epimers and resubjection of the undesired isomer to the equilibration conditions. This scalable synthetic sequence provided multi-gram quantities of 2, thus enabling the successful completion ...
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    Stereocontrolled syntheses of the C16-C28 CD-spiroacetal subunit of altohyrtin A/spongistatin 1 (1), relying on kinetic and thermodynamic control of the spiroacetal formation, are described. The kinetic control approach resulted in a slight preference (60:40) for the desired spiroacetal isomer. The thermodynamic approach allowed ready access to the desired spiroacetal 2 by acid promoted equilibration, chromatographic separation of the C23 epimers and resubjection of the undesired isomer to the equilibration conditions. This scalable synthetic sequence provided multi-gram quantities of 2, thus enabling the successful completion of the total synthesis of altohyrtin A/spongistatin 1, as reported in Part 4 of this series.
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    Journal Title
    Organic & Biomolecular Chemistry
    Volume
    3
    DOI
    https://doi.org/10.1039/b504148a
    Subject
    Medicinal and biomolecular chemistry
    Organic chemistry
    Publication URI
    http://hdl.handle.net/10072/22608
    Collection
    • Journal articles

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