Simple syntheses of lespedamine and 5-bromo-n,n-dimethyltryptamine based on 1-hydroxyindole chemistry
Heterocycles January 1, 1995 Masanori Somei, Kensuke Kobayashi, Keiko Tanii et al. 18 citations
Chemists synthesized various 1-hydroxyindoles for the first time. Using methylation or acid-catalyzed nucleophilic bromination of N,N-dimethyl-1-hydroxytryptamine, they achieved simple syntheses of lespedamine and 5-bromo-N,N-dimethyltryptamine. Lespedamine was originally isolated from Lespedeza bicolor var. japonica, and 5-bromo-N,N-dimethyltryptamine from the marine sponge Smenospongia aurea. The work supports a biosynthetic hypothesis that these compounds, along with bufotenine, may originate from N,N-dimethyl-1-hydroxytryptamine as a common intermediate. The syntheses proceeded via reduction of N,N-dimethyltryptamine to a dihydro compound, oxidation to the 1-hydroxyindole, then methylation or bromination.