Journal of the Chemical Society. Perkin transactions I p. 553 - 560 (1992)
Update date:2022-08-24
Topics:
Cooper, Jeremy
Knight, David W.
Gallagher, Peter T.
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.
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