Synthetic studies toward the first naturally occurring glutamate receptor antagonist, Kaitocephalin

ORGN 438

Rishi G. Vaswani, Deparment of Chemistry, University of California, Irvine, Irvine, CA 92697 and A. R. Chamberlin, Department of Chemistry, University of California at Irvine, Irvine, CA 92697.
As the first naturally occurring glutamate receptor antagonist, kaitocephalin provides a unique opportunity to further understand the role of (L)-glutamate in the mammalian CNS. This presentation will describe the progress toward the total synthesis of Kaitocephalin. Key transformations include the diastereoselective formation of a chiral substituted pyrrolidine ring and the stereoselective assembly of the C-4 quaternary center. To further elucidate the key structural features that contribute to antagonist activity, a small molecule library based on Kaitocephalin will also be described.