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Communication | Special issue | Vol 46, No. 1, 1997, pp.133-136
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S47
A New Route for the Tricyclic Indole System: A Useful Intermediate for Ergot Alkaloids

Yuusaku Yokoyama,* Hiroaki Matsushima, Mitsuru Takashima, Tomoko Suzuki, and Yasuoki Murakami*

*School of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan

Abstract

Cyclization of 4-bromoindole derivatives which have α,β-unsaturated esters or aldehydes in the C3-side chain, were accomplished using intramolecular palladium-catalyzed cyclization (Heck reaction) or radical cyclization using Bu3SnH and AIBN. A cyclohexa[c,d]indole system was formed by the radical reaction, while a cyclohepta[c,d]indole system was obtained using the Heck reaction.