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Communication | Regular issue | Vol 19, No. 12, 1982, pp.2269-2273
Published online, 1st January, 1970
DOI: 10.3987/R-1982-12-2269
IAC Reactions in the Indole Series: Total Synthesis of Clavicipitic Acid

Alan P. Kozikowski and Michael N. Greco

*Department of Chemistry, University of Pittsburgh, Parkman Avenue & University Drive, Pittsburgh, PA 15260 , U.S.A.

Abstract

The first total synthesis of clavicipitic acid (1), a derailment product of ergoline biosynthesis, has been accomplished through an intramolecular azide cycloaddition reaction. The 3,4-disubstituted indole required for this work was assembled from indole-4-carboxaldehyde. The single imine generated from the [3+2] cycloaddition reaction was subjected to bromination, dehydrobromination, reduction and hydrolysis to afford clavicipitic acid (~1:1 mixture of the cis and trans-isomers).