Synthesis of Functionalized Tetrahydro-β-carboline Derivatives by Modified Pictet-Spengler Reaction

Abstract

Instead of iminium salt in Pictet-Spengler reaction, a series of indole-bearing secondary enamines were synthesized through one-carbon unit transfer reactions of a tetrahydrofolate coenzyme models with tryptamine, and applied to Pictet-Spengler reaction. Reaction of the secondary enamines in acid conditions produced a series of functionalized tetrahydro-β-carboline derivatives in good to excellent yields.