HETEROCYCLES

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■ A Facile Entry to Bicyclic Systems from L-Glutamic Acid

Bryan A. Frieman, Charles W. Bock, and Krishna L. Bhat*

*Department of Chemistry, School of Science and Health, Philadelphia University, School House Lane & Henry Avenue,Philadelphia, PA 19144-5497, U.S.A.

Abstract

An efficient synthesis of bicyclic heterocycles has been realized from L-glutamic acid. The key step is the construction of the pyrrole ring in a single step, using tosylmethyl isocyanide (TosMIC) methodology. Structures of reaction intermediates and final products were investigated using density functional theory calculations.