Synthesis of the cytotoxic phytosphingosines and their isomeric analogues

Abstract

A straightforward synthesis of l-lyxo- and l-xylo-phytosphingosine along with their isomeric analogues has been accomplished. The salient features of this approach are the utilization of [3,3]-sigmatropic rearrangements to install a C-N bond and application of a late stage Wittig or OCM reaction to incorporate the hydrophobic chain unit. The final compounds were evaluated regarding their ability to alter both leukaemia and solid tumor cancer cells viability.

Keywords: Antiproliferative activity; Olefin cross-metathesis; Phytosphingosines; Sphingolipids; Stereoselective; [3,3]-sigmatropic rearrangements.