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

Abstract

Abstract 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.