Chem. Pharm. Bull., 49(1),87-96, January 2001

Regular Articles

The Chemistry of Indoles. CIII.¹⁾ 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

Masanori SOMEI,^* Fumio YAMADA, Takashi KURAUCHI, Yoshiyuki NAGAHAMA, Masakazu HASEGAWA, Koji YAMADA, Sakiko TERANISHI, Haruhiko SATO, and Chikara KANEKO

Faculty of Pharmaceutical Sciences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan.

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.

Key words 1-hydroxytryptamine; nucleophilic substitution reaction; serotonin; bufotenine; N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine; lespedamine