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Communication | Special issue | Vol 42, No. 1, 1996, pp.83-86
Published online, 1st January, 1970
DOI: 10.3987/COM-95-S25
Synthetic Studies of 1,2,3,4-Tetrahydro-1,3,4-trioxo-β-carboline Alkaloids I

Hideharu Suzuki, Kayoko Shinpo, Towako Yamazaki, Sachiko Niwa, Yuusaku Yokoyama, and Yasuoki Murakami

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

Abstract

A simple and efficient total synthesis of 1,2,3,4-tetrahydro-1,3,4-trioxo-β-carboline (1) was accomplished via C3-selective acylation of indole-2-carboxylate (5). On the course of this study, we found that the cyclization of N-(2-indolecarbonyl)glycine (8a) with PPA gave only an N-cyclized 6-membered ring (10a), whereas N-(2-indolecarbonyl)-β-alanine (8b) gave a C3-cyclized 7-membered ring (9b) as a main product.