ORGN 36

Glycosphingolipids are ubiquitous components of eukaryotic and prokaryotic organisms. They are biologically important molecules believed to be involved in all aspects of cell regulation, and cell modulation.

Plakoside A, a glycosphingolipid isolated from a marine sponge Plakortis simplex has been shown to possess immunosuppressive activity. Moreover, studies show it to be inactive in MTT assay for cytotoxicity. Thus, plakoside A may represent a novel, non-cytotoxic class of immunosuppressants with potential therapeutic applications, and, as such, is a significant synthetic target. Key features of our strategy involve Charette cyclopropanation and asymmetric cyanohydrin reaction for the construction of the a-hydroxy acid. The synthesis of plakoside A utilizing novel methodology from 1 will be presented.