Total synthesis of (–)-α-kainic acid
- 1 January 1992
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 5,p. 553-559
- https://doi.org/10.1039/p19920000553
Abstract
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.Keywords
This publication has 2 references indexed in Scilit:
- Studies on the Active Components of Digenea simplex Ag. and Related Compounds.Proceedings of the Japan Academy, 1957
- Studies on the Active Components of Digenea simplex Ag. and Related Compounds.Proceedings of the Japan Academy, 1957