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Communication | Special issue | Vol 13, No. 1, 1979, pp.209-215
Published online, 1st January, 1970
DOI: 10.3987/S-1979-01-0209
Studies on the Syntheses of Heterocyclic Compounds. Part 808. Total Synthesis of (±)-O-Methyltubulosine

Tetsuji Kametani,* Yukio Suzuki, and Masataka Ihara

*Pharmaceutical Institute, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan

Abstract

Pictet-Spengler condensation of (±)-4-oxoprotoemetine (5) with 5-methoxytryptamine (10) in acetic acid gave (±)-4-oxo-O-methyltubulosine (12a) which was converted to (±)-O-methyltubulosine (13a) by reduction with sodium bis(2-methoxyethoxy)-aluminium hydride. Modified syntheses of (±)-4-oxoprotoemetine (5) and (±)-protoemetine (9) are also described.