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Paper | Special issue | Vol 59, No. 2, 2003, pp.527-540
Published online, 1st January, 1970
DOI: 10.3987/COM-02-S50
Total Synthesis of Lennoxamine and Chilenine via Ring-Expansion of Isoindoloisoquinoline to Isoindolobenzazepine

Yuji Koseki, Shinya Katsura, Shuichi Kusano, Harumi Sakata, Hiroto Sato, Yoshinori Monzene, and Tatsuo Nagasaka*

*Tokyo University of Pharmacy and Life Science, School of Pharmacy, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

Convenient synthesis of the benzazepine alkaloids, lennoxamine (1) and chilenine (2), is described. The key steps are conversion of methylenelactam (5) to an N-tertiary acyliminium ion precursor (16) and a novel expansion of the six-membered ring of 4 to a benzazepine ring system (3b), which could be transformed into lennoxamine (1) and chilenine (2).