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Communication | Special issue | Vol 15, No. 1, 1981, pp.207-212
Published online, 1st January, 1970
DOI: 10.3987/S-1981-01-0207
Reactions and Synthetic Applications of β-Keto Sulfoxides IX. Synthesis of 5-Methylthio and 5-Methoxy Analogs of Ellipticine

Yuji Oikawa, Masahide Tanaka, Hitoshi Hirasawa, and Osamu Yonemitsu*

*Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12 Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan

Abstract

A β-keto sulfoxide (9) derived from ethyl indole-butyrate (8) and FAMSO was cyclized to a 2-keto-1,2,3,4-tetrahydrocarbazole derivative (10). After introduction of an acetic ester at the carbonyl group to give 11, its aromatization gave a 1-methylthiocarbazole (12), followed by construction of a pyridine ring to yield efficiently 5-methylthioellipticine (6). Compound 11 was quite easily hydrolyzed to a 1-keto derivative (18), which was aromatized and then converted to 5-methoxyellipticine (7).