Title
A formal synthesis of the glycosphingolipid, plakoside A
Date of Completion
January 2004
Keywords
Chemistry, Organic|Chemistry, Pharmaceutical
Degree
Ph.D.
Abstract
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 an 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. A formal synthesis of plakoside A is presented. Key features of our strategy include the use of Charette asymmetric cyclopropanation and enzyme catalyzed dynamic kinetic resolution. The synthesis of the sphingoid base exploits a serine-derived Weinreb amide, while the acyl chain is built from cyclooctadiene. ^
Recommended Citation
So, Regina Cheng, "A formal synthesis of the glycosphingolipid, plakoside A" (2004). Doctoral Dissertations. AAI3123469.
https://digitalcommons.lib.uconn.edu/dissertations/AAI3123469