Asymmetric total synthesis of MK8383: the iron-mediated coupling reaction is the only effective method for the construction of the (Z)-trisubstituted side-chain alkene

Nobuyuki Hayashi, Masahisa Nakada

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    10 Citations (Scopus)

    Abstract

    The first asymmetric total synthesis of MK8383 through the iron-mediated coupling reaction is described. In this total synthesis, the key step was clearly the stereoselective construction of the (Z)-trisubstituted side-chain alkene. Although this problem was seemingly easy to resolve, in fact it presented us an opportunity to evaluate the coupling reactions reported to date, and the iron-mediated coupling reaction was found to be the only effective method for the stereoselective construction of the (Z)-trisubstituted side-chain alkene.

    Original languageEnglish
    Pages (from-to)232-235
    Number of pages4
    JournalTetrahedron Letters
    Volume50
    Issue number2
    DOIs
    Publication statusPublished - 2009 Jan 14

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    Alkenes
    Iron

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

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    abstract = "The first asymmetric total synthesis of MK8383 through the iron-mediated coupling reaction is described. In this total synthesis, the key step was clearly the stereoselective construction of the (Z)-trisubstituted side-chain alkene. Although this problem was seemingly easy to resolve, in fact it presented us an opportunity to evaluate the coupling reactions reported to date, and the iron-mediated coupling reaction was found to be the only effective method for the stereoselective construction of the (Z)-trisubstituted side-chain alkene.",
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    AB - The first asymmetric total synthesis of MK8383 through the iron-mediated coupling reaction is described. In this total synthesis, the key step was clearly the stereoselective construction of the (Z)-trisubstituted side-chain alkene. Although this problem was seemingly easy to resolve, in fact it presented us an opportunity to evaluate the coupling reactions reported to date, and the iron-mediated coupling reaction was found to be the only effective method for the stereoselective construction of the (Z)-trisubstituted side-chain alkene.

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