title: DMSO/Tf2O-mediated cross-coupling of tryptamine with substituted aniline to access C3a-N1'-linked pyrroloindoline alkaloids.
abstract: The cross-coupling of tryptamine with substituted aniline to access C3a-nitrogen-linked pyrroloindolines has been developed via the consecutive cyclization of tryptamine with DMSO/Tf2O and the substitution of 3a-pyrroloindolylthionium intermediate with aniline. The use of 2,3-dihydrotryptamine instead of aniline enabled easy access to 3a-(1-indolyl)pyrroloindoline and the concise synthesis of C3a-N1'-linked pyrroloindoline alkaloid (±)-psychotriasine was accomplished.
authors.affiliation: Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan. khiguchi@my-pharm.ac.jp kawasaki@my-pharm.ac.jp.
authors.forename: Masanori
authors.initials: M
authors.lastname: Tayu
authors.forename: Takako
authors.initials: T
authors.lastname: Ishizaki
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Higuchi
authors.forename: Tomomi
authors.initials: T
authors.lastname: Kawasaki
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry*; D004121:Dimethyl Sulfoxide / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D013237:Stereoisomerism; D014363:Tryptamines / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D000814:Aniline Compounds; D007211:Indoles; D008698:Mesylates; D014363:Tryptamines; C030820:tryptamine; C012077:trifluoromethanesulfonic acid; C023650:aniline; D004121:Dimethyl Sulfoxide