title: Total Synthesis of cis-Clavicipitic Acid from Asparagine via Ir-Catalyzed C-H bond Activation as a Key Step.
abstract: 4-Substituted tryptophan derivatives and the total synthesis of cis-clavicipitic acid were achieved in reactions in which Ir-catalyzed C-H bond activation was a key step. The starting material for these reactions is asparagine, which is a cheap natural amino acid. The reductive amination step from the 4-substituted tryptophan derivative gave cis-clavicipitic acid with perfect diastereoselectivity.
authors.affiliation: Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo 169-8555(Japan).
authors.forename: Yu-ki
authors.initials: YK
authors.lastname: Tahara
authors.affiliation: Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo 169-8555(Japan).
authors.forename: Mamoru
authors.initials: M
authors.lastname: Ito
authors.affiliation: International Center for Science and Engineering Programs (ICSEP), Waseda University, Shinjuku, Tokyo 169-8555 (Japan).
authors.forename: Kyalo Stephen
authors.initials: KS
authors.lastname: Kanyiva
authors.affiliation: Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo 169-8555(Japan). tshibata@waseda.jp.|ACT-C (Japan) Science and Technology Agency (JST), 4-1-8 Honcho Kawaguchi, Saitama, 332-0012 (Japan). tshibata@waseda.jp.
authors.forename: Takanori
authors.initials: T
authors.lastname: Shibata
mesh_terms: D000586:Amination; D000596:Amino Acids / Q000737:chemistry*; D001216:Asparagine / Q000737:chemistry*; D002384:Catalysis; D004876:Ergot Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D006860:Hydrogen Bonding; D007495:Iridium / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014364:Tryptophan / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D004876:Ergot Alkaloids; C524935:clavicipitic acid; D007495:Iridium; D001216:Asparagine; D014364:Tryptophan
keywords: 4-substituted tryptophan derivatives; CH activation; clavicipitic acid; iridium; total synthesis