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.
- 1 January 2001
- journal article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 49 (1) , 87-96
- https://doi.org/10.1248/cpb.49.87
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.Keywords
This publication has 33 references indexed in Scilit:
- Syntheses of 1-Hydroxytryptamines and Serotonins Having Fattyacyl or (E)-3-Phenylpropenoyl Derivatives as an Nb-Substituent, and a Novel Homologation on the 3-Substituent of the 1-Hydroxytryptamines upon Treatment with DiazomethaneHETEROCYCLES, 1998
- Indole Alkaloids fromAntirhea lucidaPlanta Medica, 1995
- The chemistry of indoles. Part 57. The chemistry of 1-hydroxyindoles: Syntheses of methyl 1-hydroxyindole-3-acetate, Nb-acetyl-1-hydroxytryptamine, (-)- and (S)-1-hydroxytryptophan derivatives.CHEMICAL & PHARMACEUTICAL BULLETIN, 1991
- Selective Monoalkylation of Carbon Nucleophiles with GramineHETEROCYCLES, 1981
- Stereoselective reduction of some indoles with triethylsilane-trifluoroacetic acidThe Journal of Organic Chemistry, 1979
- Über Alkaloide, V Inhaltsstoffe von Lespedeza bicolor var. japonica, I. über Lespedamin, ein neues AlkaloidEuropean Journal of Organic Chemistry, 1965
- ISOLATION OF MELATONIN, THE PINEAL GLAND FACTOR THAT LIGHTENS MELANOCYTES1Journal of the American Chemical Society, 1958
- Cyclic Hydroxamic Acids Derived from IndoleJournal of the American Chemical Society, 1956
- The Isolation of Bufotenine from Piptadenia peregrinaJournal of the American Chemical Society, 1954
- Über das Vorkommen von Bufotenin im gelben KnollenblätterpilzEuropean Journal of Organic Chemistry, 1953