A novel, efficient synthesis of (±)-erythro-sphingosine

Article abstract of DOI:10.1016/S0040-4020(01)87498-6

A stereoselective synthesis of (±)-erythro-sphingosine triacetate (1) is described. The key reaction that determines the right stereochemistry is the iodocyclization of 1-trichloroacetimido-(2E,4E)-octadecadiene (5). The 4,5-dihydro-1,3-oxazine (6) through cleavage with HCl and treatment with Amberlyst A 26 in the AcO^- form, followed by full acetylation, affords (1) in good yield.