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

Authors
Somei, M Yamada, F Kurauchi, T Nagahama, Y Hasegawa, M Yamada, K Teranishi, S Sato, H Kaneko, C
Citation
M. Somei et al., 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, CHEM PHARM, 49(1), 2001, pp. 87-96
Citations number
42
Categorie Soggetti
Chemistry & Analysis
Journal title
CHEMICAL & PHARMACEUTICAL BULLETIN
ISSN journal
00092363 → ACNP
Volume
49
Issue
1
Year of publication
2001
Pages
87 - 96
Database
ISI
SICI code
0009-2363(200101)49:1<87:TCOICS>2.0.ZU;2-C
Abstract
Application of regioselective nucleophilic substitution reactions of 1-hydr oxytryptamines to novel and simple syntheses of serotonin (1a), N-methylser otonin (1b), bufotenine (1c), 5-methoxy-N-methyltryptamine (2a), bufobutano ic acid (3a), N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine (4), and le spedamine (5) are described. Effective syntheses of 5-benzyloxytryptamine a nd 1-methoxy-2-oxindoles are also reported.