Pravat Mondal, N. Argade
Jul 11, 2014
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Journal
Synthesis
Abstract
A facile convergent access to the important indole alkaloid (+)-harmicine is described, starting from tryptamine and ( R )-acetoxysuccinic anhydride via the corresponding acetoxysuccinimide in very good overall yield. Regioselective reduction of an unsymmetrical imide carbonyl group and acid-catalyzed stereoselective intramolecular cyclization were the key features involved. The directing group to induce asymmetry was finally detached via the corresponding iodide by using tributyltin hydride chemistry.