title: A Diels-Alder-based total synthesis of (-)-kainic acid.
abstract: An efficient synthesis of (-)-kainic acid, through a high-pressure-promoted Diels-Alder cycloaddition of a vinylogous malonate derived from 4-hydroxyproline, is described. The bicyclic adduct could be converted into the natural product with complete stereocontrol.
authors.affiliation: Département de Chimie Moléculaire (SERCO) CNRS, UMR-5250, ICMG FR-2607, Université Joseph Fourier BP-53, 38041 Grenoble Cedex 9, France.
authors.forename: Arturo
authors.initials: A
authors.lastname: Orellana
authors.forename: Sushil K
authors.initials: SK
authors.lastname: Pandey
authors.forename: Sébastien
authors.initials: S
authors.lastname: Carret
authors.forename: Andrew E
authors.initials: AE
authors.lastname: Greene
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Poisson
mesh_terms: D003500:Cyclization; D006909:Hydroxyproline / Q000737:chemistry; D007608:Kainic Acid / Q000138:chemical synthesis* / Q000737:chemistry; D008314:Malonates / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D008314:Malonates; C030290:malonic acid; D006909:Hydroxyproline; D007608:Kainic Acid