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Paper | Regular issue | Vol 60, No. 4, 2003, pp.791-798
Published online, 4th February, 2003
DOI: 10.3987/COM-02-9679
Synthesis of Chiral 3,4-Disubstituted Pyrroles from L-Amino Acids

Jocelyn A. Hover, Charles W. Bock, and Krishna L. Bhat*

*Department of Chemistry and Biochemistry, School of Science and Health, Philadelphia University, Philadelphia, PA 19144, U.S.A.

Abstract

A general methodology for the conversion of naturally occurring amino acids to 3,4-disubstituted pyrroles is described. A suitably protected amino acid (1) was first converted to the corresponding aldehyde (2). Horner-Emmons olefination afforded a facile entry to the corresponding α,β-unsaturated ester (3). The construction of the pyrrole ring system was accomplished in a single step, using an intramolecular cyclization reaction with tosylmethyl isocyanide (TOSMIC).