Regio- and Stereoselective Incorporation of a 13<i>C</i> Nuclide into <scp>d</scp>-<i>ribo</i>-Phytosphingosine <i>via</i> SmI2-Mediated C–C Formation with 13<i>C</i>-Labeled Isocyanide

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  • Masahiro Murakami
    Department of Synthetic Chemistry and Biological Chemistry, Faculty of Engineering, Kyoto University
  • Hajime Ito
    Department of Synthetic Chemistry and Biological Chemistry, Faculty of Engineering, Kyoto University
  • Yoshihiko lto
    Department of Synthetic Chemistry and Biological Chemistry, Faculty of Engineering, Kyoto University

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Abstract

<jats:title>Abstract</jats:title> <jats:p>Preparation of a 13C-labeled isocyanide and its application to the total synthesis of [2-13C]d-ribo-C18-phytosphingosine are described. The synthesis of the labeled phytosphingosine is based on the use of the isocyanide as a 13CH–NH2 precursor in the SmI2-mediated three-component coupling reaction, wherein regio- and stereoselective incorporation of a 13C nuclide in the carbon skeleton is achieved.</jats:p>

Journal

  • Chemistry Letters

    Chemistry Letters 25 (3), 185-186, 1996-03-01

    Oxford University Press (OUP)

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