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Paper | Regular issue | Vol 32, No. 12, 1991, pp.2389-2397
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5856
Synthesis of Fused Aminotetrahydrocarbazole Compounds

Yasuo Shimoji,* Fujio Saito, Kuniyuki Tomita, and Yasuhiro Morisawa

*Sankyo Research Laboratories, Sankyo Co., Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan

Abstract

Intramolecular Diels-Alder reaction of 3-(1H-indol-3-yl)-2-propenoates having olefinic substituents at the 1-position of the indole ring gave stereoselectively pentacyclic fused indole compounds in good yield. Aminotetrahydrocarbazoles derivatives (8, 21, 22) were obtained by Curtius rearrangement via carboxylic acid derivatives. Some of these compounds showed interesting pharmacological activity such as antiarrhythmic activity.