‘Chiron’ approach to stereoselective synthesis of sphinganine and unnatural safingol, an antineoplastic and antipsoriatic agent

Abstract

Highly stereoselective total syntheses of sphingoid bases, natural bioactive ceramide sphinganine 1 (with an overall yield of 33%) and unnatural antineoplastic and antipsoriatic drug safingol 17 (with an overall yield of 38%) starting from chirons 3,4,6-tri-O-benzyl-D-galactal and 3,4,6-tri-O-benzyl-D-glucal respectively have been demonstrated. Mitsunobu reaction and late stage olefin cross metathesis are utilized as important steps in order to complete the total synthesis of these sphingoid molecules.