A practical synthesis of L-threo-dihydrosphingosine (safingol), an antineoplastic and antipsoriatic agent

Abstract

L S -threo-Dihydrosphingosine, an antineoplastic and antipsoriatic drug, has been synthesized by the Henri reaction of hexadecanal and 2-nitroethanol followed by catalytic hydrogenation of the dl-threo-2-nitro-1,3-octadecanediol and resolution of the racemic dl-threo-dihydrosphingosine. Selection of solvents for recrystallization of mixtures of dl-threo and erythro diastereoisomers proved to be of critical importance for the 100-gram scale preparation of the target compound.