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N-Alkylation of the β-amino acid derivative 16, derived from (L)-aspartic acid, by the allylic chloride 12b followed by deprotection and lactonization leads to the nine-membered azalactone 18. Enolate Claisen rearrangement of this leads stereospecifically, via a boat-like transition state (cf. 6), to the pyrrolidine acid 19; subsequent one-carbon homologation, oxidation and deprotection affords (–)-(α)-kainic acid 1.
J. Cooper, D. W. Knight and P. T. Gallagher, J. Chem. Soc., Perkin Trans. 1, 1992, 553 DOI: 10.1039/P19920000553
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