Regio- and stereocontrolled synthesis ofD-erythrosphingosine and phytosphingosine fromDglucosamine

Article abstract of DOI:10.1016/S0040-4039(00)75806-0

D-erythro-Sphingosine (1) and phytosphingosine (2) have been efficiently synthesized from _D-glucosamine by utilizing its whole carbon skeleton and functional groups. In this synthetic route, regioselective alkylation of the epoxy-tosylate 9 was achieved with a copper(I)-catalyzed Grignard reagent to give the key intermediate 10, which was converted to both 1 and 2 via regioselective formation of the iodohydrin 11.