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Paper | Special issue | Vol 56, No. 1-2, 2002, pp.313-330
Published online, 1st January, 1970
DOI: 10.3987/COM-01-S(K)42
Synthesis of 2,3-Disubstituted Indoles by Radical Cyclization with Hypophosphorous Acid and Its Application to Total Synthesis of (±)-Catharanthine

Matthew T. Reding, Yosuke Kaburagi, Hidetoshi Tokuyama, and Tohru Fukuyama*

*Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

Abstract

Radical cyclization of o-alkenylthioanilides using hypophosphorous acid and AIBN in the presence of Et3N proceeded smoothly to furnish the corresponding 2,3-disubstituted indoles in high yields. Utilizing the newly developed cyclization condition, a stereocontrolled total synthesis of (±)-catharanthine has been completed.