Stereoselective syntheses of D-ribo- and L-lyxo-phytosphingosine

Abstract

D-ribo-Phytosphingosine has been synthesized from D-galactose via the key intermediate 5, itself prepared by stereoselective prop-2-ynylation with prop-2-ynyl bromide and zinc, and L-lyxo-phytosphingosine has been synthesized from D-xylose via the key intermediate 18, itself prepared by a CBr4–Ph3P–Zn Wittig reaction and debromination. These key chiral intermediates, 5 and 18, have potential as intermediates for the synthesis of other phytosphigosine derivatives.