A versatile linkage strategy for solid-phase synthesis of N,N-dimethyltryptamines and beta-carbolines.
Various tryptamines are captured by a vinylsulfonylmethyl polystyrene resin, generating a safety-catch linkage. Beta-carbolines can be formed from 4 by a Pictet-Spengler reaction with the introduction of R(1). Tryptamine 4 can also be derivatized by acylation or copper-mediated coupling to introduce R(2). If X = Br, Suzuki coupling can be used to introduce R(3). After derivatization, the indole derivatives are activated with methyl iodide and released under mild basic condition. [reaction: see text]
Wu
Tom Y H
TY
Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
Schultz
Peter G
PG
D002243:Carbolines / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D004130:N,N-Dimethyltryptamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
D002243:Carbolines; D007202:Indicators and Reagents; D004130:N,N-Dimethyltryptamine