title: Strategies for the Total Synthesis of Clavicipitic Acid.
abstract: Clavicipitic acid is an ergot alkaloid, which was isolated from Claviceps strain and Claviceps fusiformis. Its unique tricyclic azepinoindole skeleton has attracted synthetic chemists, and various strategies have been developed for its total synthesis. These strategies can be generally categorized into two types based on the synthetic intermediates, namely, 4-substituted gramine derivatives and 4-substituted tryptophan derivatives. This Minireview summarizes the reported total syntheses from the point of these two key intermediates.
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: 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. 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: D002384:Catalysis; D004876:Ergot Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014364:Tryptophan / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D004876:Ergot Alkaloids; C524935:clavicipitic acid; D014364:Tryptophan
keywords: azepinoindole; clavicipitic acid; gramine; total synthesis; tryptophan