title: The chemistry of indoles. CIII. Simple syntheses of serotonin, N-methylserotonin, bufotenine, 5-methoxy-N-methyltryptamine, bufobutanoic acid, N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine, and lespedamine based on 1-hydroxyindole chemistry.
abstract: Application of regioselective nucleophilic substitution reactions of 1-hydroxytryptamines to novel and simple syntheses of serotonin (1a), N-methylserotonin (1b), bufotenine (1c), 5-methoxy-N-methyltryptamine (2a), bufobutanoic acid (3a), N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine (4), and lespedamine (5) are described. Effective syntheses of 5-benzyloxytryptamine and 1-methoxy-2-oxindoles are also reported.
authors.affiliation: Faculty of Pharmaceutical Sciences, Kanazawa University, Japan. somei@dbs.p.kanazawa-u.ac.jp
authors.forename: M
authors.initials: M
authors.lastname: Somei
authors.forename: F
authors.initials: F
authors.lastname: Yamada
authors.forename: T
authors.initials: T
authors.lastname: Kurauchi
authors.forename: Y
authors.initials: Y
authors.lastname: Nagahama
authors.forename: M
authors.initials: M
authors.lastname: Hasegawa
authors.forename: K
authors.initials: K
authors.lastname: Yamada
authors.forename: S
authors.initials: S
authors.lastname: Teranishi
authors.forename: H
authors.initials: H
authors.lastname: Sato
authors.forename: C
authors.initials: C
authors.lastname: Kaneko
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D012701:Serotonin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D013057:Spectrum Analysis; D014363:Tryptamines / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D007211:Indoles; D014363:Tryptamines; D012701:Serotonin; C030820:tryptamine