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  • An Efficient Stereoselective Synthesis of a Racemic CD-intermediate of Vitamin D

    Author(s)
    Loughlin, Wendy
    Haynes, Richard K.
    Griffith University Author(s)
    Loughlin, Wendy A.
    Year published
    1995
    Metadata
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    Abstract
    A highly efficient four-step approach to the racemic CD-intermediate 8 from the racemic hydrindenone 10 has been developed. In the key step, the hydrindenone 10 is converted stereoselectively into the (±)-bromohydrindenone 17. Oxygen transposition from C-9 to C-8 is effected by means of conversion of 17 to the epoxide 20 and regioselective reductive ring opening of 20 with DIBALH. The resulting (±)-hydrindanol 8 was converted by the Homer—Wittig reaction with -methacrolein into the diene 24, hydrogenation of which provided the racemic hydrindanol 25. This is a direct precursor of racemic Grundmann’s ketone 9 and bears the ...
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    A highly efficient four-step approach to the racemic CD-intermediate 8 from the racemic hydrindenone 10 has been developed. In the key step, the hydrindenone 10 is converted stereoselectively into the (±)-bromohydrindenone 17. Oxygen transposition from C-9 to C-8 is effected by means of conversion of 17 to the epoxide 20 and regioselective reductive ring opening of 20 with DIBALH. The resulting (±)-hydrindanol 8 was converted by the Homer—Wittig reaction with -methacrolein into the diene 24, hydrogenation of which provided the racemic hydrindanol 25. This is a direct precursor of racemic Grundmann’s ketone 9 and bears the alkyl side chain and the correct relative configuration at C13, C14, C17, and C20 of Vitamin D.
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    Journal Title
    Journal of Organic Chemistry
    Volume
    60
    Issue
    4
    DOI
    https://doi.org/10.1021/jo00109a009
    Subject
    Chemical Sciences
    Medicinal and Biomolecular Chemistry
    Organic Chemistry
    Publication URI
    http://hdl.handle.net/10072/120255
    Collection
    • Journal articles

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