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Asymmetric Reduction of Diynones and the Total Synthesis of (S)-Panaxjapyne A

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    Asymmetric Reduction of Diynones and the Total Synthesis of (S)-Panaxjapyne A
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    Department of Chemistry, The University of Warwick, Coventry, CV4 7AL, U.K.
    *E-mail: [email protected]
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    Organic Letters

    Cite this: Org. Lett. 2014, 16, 2, 374–377
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    https://doi.org/10.1021/ol4032123
    Published December 30, 2013
    Copyright © 2013 American Chemical Society
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    Abstract

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    The asymmetric transfer hydrogenation of a series of diynones has been achieved in high conversion and enantiomeric induction. When R1 is a phenyl group, a competing alkyne reduction takes place; however, when R1 is an alkyl group, this side-reaction is not observed. The application of the reduction to the total synthesis of the natural product (S)-panaxjapyne A in high enantiomeric excess is described.

    Copyright © 2013 American Chemical Society

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    Organic Letters

    Cite this: Org. Lett. 2014, 16, 2, 374–377
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ol4032123
    Published December 30, 2013
    Copyright © 2013 American Chemical Society
    Request reuse permissions

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