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, alpha-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(N)2 type reaction. a-Hydroxy acid was prepared from (R)4-hydroxytetrahydrofuran-2-one, which in turn could be obtained from L-ascorbic add.