Progress in the Synthesis of (−)-α-Kainic Acid

Abstract

Causing neuronal death, kainic acid and its derivatives are toxic to several known animal species, including rats. Kainic acid and its derivatives have been shown to cause neuroexcitatory activity observed in several neurological disorders. In this research project, a synthetic route that involves control of the stereochemistry to synthesize a pure stereoisomer of kainic acid is proposed. The pure stereoisomer possesses certain medical properties of interest to pharmacological companies. This laboratory synthesis is gaining popularity and increasing importance all over the world because extraction from seaweeds, where kainic acid is found, does not produce reasonable yields. This laboratory procedure will attempt to synthesize kainic acid using an ENE reaction in the final step of the 12 steps as shown in the graphical abstract.

Keywords:

• ENE reaction
• kainic acid
• OBO protecting group

ACKNOWLEDGMENTS

We thank the University of South Carolina (USC) for offering us partial funding for this project through the Magellan Scholar program and the University of South Carolina–Aiken (USCA) for startup funding. We also thank the NMR facility staff at USC in Columbia for running almost all our NMR samples.