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Paper | Special issue | Vol 67, No. 2, 2006, pp.643-653
Published online, 27th September, 2005
DOI: 10.3987/COM-05-S(T)38
Synthesis of Highly Substituted Indole Alkaloid Species via [4+1] Cyclization of Nucleophilic Carbenes and Indole Isocyanates

James H. Rigby* and Patrick J. Burke

*Department of Chemistry, Wayne State University, Detroit, MI 49202-3489, U.S.A.

Abstract

Thermally induced [4 + 1] cyclization between indole isocyanates and dimethoxycarbene or bis(propylthio)carbene has been achieved with good chemical efficiency. The methodology provides rapid access to fused pyrroloindole substructures commonly found in a variety of indole alkaloid natural products.