Stereocontrolled Synthesis of (+)-Methoxyphenylkainic Acid and (+)-Phenylkainic Acid
journal contributionposted on 04.03.2011 by Takumi Higashi, Yoichiro Isobe, Hitoshi Ouchi, Hiroto Suzuki, Yuko Okazaki, Tomohiro Asakawa, Takumi Furuta, Toshiyuki Wakimoto, Toshiyuki Kan
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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.