Synthesis of a New Cerebroside Isolated from Typhonium giganteum Engl^†

The stereoselective synthesis of typhoniside, a new cerebroside isolated from Typhonium giganteum Engl, was accomplished. Cerebrosides are a kind of glycolipids highly enriched on the surface of myelin-producing cells and are composed by C18–4, 8-sphingadienine, α-hydroxy acid and a saccharide head. It was the first time that cerebrosides were isolated from this traditional Chinese medicine (TCM) by us. In this paper, C18–4, 8-sphingadienine was synthesized from D-xylose via a S_N2 type reaction, α-Hydroxy acid was prepared from (R)-4-hydroxyte-trahydrofuran-2-one, which in turn could be obtained from L-ascorbic acid.