Stereocontrolled synthesis of 5α- and 5β-substituted kainic acids
Journal of Organic Chemistry, ISSN: 0022-3263, Vol: 64, Issue: 12, Page: 4304-4314
1999
- 21Citations
- 6Captures
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Article Description
A general and efficient method for the stereoselective synthesis of racemic 5β- and 5α-substituted kainic acids 3 and 4 has been developed starting from the bicyclic pyroglutamate derivative 6, readily available on a large scale. Compound 6 proved to be a versatile synthon from which straightforward functionalizations at both C-5β and C-5α were accomplished in a stereoselective manner without compromising the stereogenic integrity of the potentially labile C-2 center. The key steps involved the stereoselective nucleophilic addition of organocopper reagents to the N-acyliminium ion I, and the stereoselective hydrogenation of the cyclic imine 9 derived from 6. Transformations of the bicyclic intermediates 7 and 8 into the final substituted kainic acids 3 and 4 were accomplished via stepwise sequences that avoid the facile and undesirable intramolecular Claisen and epimerization reactions. Compounds 3 and 4 have shown no significant binding affinity for the kainate receptors, which reflects the sensitivity of the recognition site to steric and conformational factors.
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