title: Stereocontrolled synthesis of (+)-methoxyphenylkainic acid and (+)-phenylkainic acid.
abstract: The efficient total syntheses of (+)-methoxyphenylkainic acid (3) and (+)-phenylkainic acid (4) were achieved using a rhodium carbenoid-mediated intermolecular C-H insertion reaction. Complete stereoselective construction of the kainoid skeleton was accomplished by utilizing the stereochemistry at the C-4 position as a pivotal stereogenic center.
authors.affiliation: School of Pharmaceutical Sciences, University of Shizuoka and Global COE Program, Suruga-ku, Shizuoka, Japan.
authors.forename: Takumi
authors.initials: T
authors.lastname: Higashi
authors.forename: Yoichiro
authors.initials: Y
authors.lastname: Isobe
authors.forename: Hitoshi
authors.initials: H
authors.lastname: Ouchi
authors.forename: Hiroto
authors.initials: H
authors.lastname: Suzuki
authors.forename: Yuko
authors.initials: Y
authors.lastname: Okazaki
authors.forename: Tomohiro
authors.initials: T
authors.lastname: Asakawa
authors.forename: Takumi
authors.initials: T
authors.lastname: Furuta
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Wakimoto
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Kan
mesh_terms: D007608:Kainic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C557759:methoxyphenylkainic acid; C557758:phenylkainic acid; D012238:Rhodium; D007608:Kainic Acid