title: [Synthesis of indole compounds using multifunctional synthons].
abstract: This review describes a synthesis of indole compounds using multifunctional synthons. The multifunctional synthons, trienes and gramines, were respectively synthesized using Pd-catalyzed tandem cyclization/cross-coupling reaction of indolylborate with vinyl bromide, and reaction of indolylcuprate with iminium chloride. As an application of the multifunctional synthons to the indole alkaloids synthesis, we accomplished the total synthesis of ellipticine, 9-methoxyellipticine, 9-hydroxyellipticine, tetrahydroellipticine, μ-alkaloid B, μ-alkaloid D, calothrixin A, calothrixin B, tubifoline, and yuehchukene. We have also developed 6π-electrocyclization of hexatrienes catalyzed by Cu(I) trifluoromethanesulfonate toluene complexe, which is unprecedented.
authors.affiliation: Faculty of Pharmaceutical Sciences, Health Science University of Hokkaido, Japan. abe-t@hoku-iryo-u.ac.jp
authors.forename: Takumi
authors.initials: T
authors.lastname: Abe
mesh_terms: D000470:Alkaloids; D002130:Calcium Phosphates / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D003300:Copper; D003500:Cyclization; D007097:Imines; D026121:Indole Alkaloids; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008698:Mesylates; D010165:Palladium / Q000737:chemistry; D014753:Vinyl Compounds
chemical_list: D000470:Alkaloids; D002130:Calcium Phosphates; D007097:Imines; D026121:Indole Alkaloids; D007211:Indoles; D008698:Mesylates; D014753:Vinyl Compounds; C485817:beta-tricalcium phosphate; D010165:Palladium; D003300:Copper; C003763:vinyl bromide; C007884:gramine; C012077:trifluoromethanesulfonic acid