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Report | Regular issue | Vol 23, No. 7, 1985, pp.1671-1673
Published online, 1st January, 1970
DOI: 10.3987/R-1985-07-1671
Synthesis of N(2)-Hydroxy-1,2,3,4-tetrahydro-β-carbolines

So-Yeop Han, M. V. Lakshmikantham, and Michael P. Cava*

*Department of Chemistry, University of Pennsylvania, 231 South 34th Street Philadelphia, PA 19104-6323, U.S.A.


N-Hydroxytryptamine condensed readily with a series of aldehydes in the presence of a catalytic amount of acetic acid to give the corresponding nitrones (4a-f), which in turn were cyclized by hydrochloric acid to the stable N(2)-hydroxytetrahydro-β-carbolines (5a-f). β-Carbolines of this type have not previously been synthesized, and are of interest because of their structural relationship to several potent antiviral marine alkaloids (eudistomins C, E, K and L).