ORGN 737 |
| (–)-Kainic acid (1), isolated from marine alga, is the parent member of the kainoids that display potent anthelmintic properties. Since kainic acid also acts as a strong agonist for glutamate receptors, this compound has been widely used as a useful tool in the field of neuropharmacology. Despite its continued demand, a supply of the natural kainic acid is diminishing due to overharvest. Under this circumstance, we are pursuing studies to develop a practical synthetic route to 1. Our synthesis features a ring-closing metathesis of the optical active acrylate derivative 2 and an intramolecular Michael addition reaction of the resultant a,b-unsaturated lactone 3 as the key processes. The latter reaction proceeded smoothly to provide the fully functionalized pyrroridine derivative 4 in high diastereoselectivity. In this paper, we discuss the detailed preparation of 2 as well as an alternative protocol to form the lactone 3.
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Total Synthesis, Materials, Molecular Recognition, Process R&D, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 13 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |
