title: Short total synthesis of (-)-kainic acid.
abstract: A short total synthesis of (-)-kainic acid has been developed involving a novel diastereofacial differentiating Cu-catalyzed Michael addition-cyclization reaction, which provided access to a chiral pyrroline in a highly stereoselective manner. The chiral pyrroline was converted to (-)-kainic acid via the stereoselective 1,4-reduction of the pyrroline double bond in three steps.
authors.affiliation: Graduate School of Science, Osaka City University , Sugimoto, Sumiyoshi, Osaka 558-8585, Japan.
authors.forename: Kentaro
authors.initials: K
authors.lastname: Oe
authors.forename: Yasufumi
authors.initials: Y
authors.lastname: Ohfune
authors.forename: Tetsuro
authors.initials: T
authors.lastname: Shinada
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry; D007608:Kainic Acid / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011758:Pyrroles / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D011758:Pyrroles; C013231:pyrroline; D003300:Copper; D007608:Kainic Acid