Electrochemistry of Natural Products. 7. Oxidative Decarboxylation of Some Tetrahydro-β-carbolinecarboxylic Acids

Article abstract of DOI:10.1021/jo01298a045

A series of 1,2,3,4-tetrahydro-β-carboline-1- and -3-carboxylic acids containing various substituents in positions 1, 2, and 3 were oxidized electrochemically.In general, the acids were decarboxylated, and unsaturation was introduced into the C ring.The oxidation appears to take place through the indole ring nitrogen, and possible mechanisms of the reactions are presented.Parallels between the observed reactions and early steps in indole alkaloid biosynthesis are discussed.The oxidative dimerization of tetrahydrocarbazole is reported.