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Paper | Regular issue | Vol 24, No. 12, 1986, pp.3385-3395
Published online, 1st January, 1970
DOI: 10.3987/R-1986-12-3385
Application of the Lewis Acid Catalyzed [4+2]Cycloaddition Reaction to Synthesis of Natural Quinoline Alkaloids

Tetsuji Kametani,* Hajime Takeda, Yukio Suzuki, Hiroko Kasai, and Toshio Honda

*Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan

Abstract

Lewis acid catalyzed [4+2]cycloaddition reaction of the Schiff base with the olefin was applied to the syntheses of some natural quinoline alkaloids. The extension of [4+2]cycloaddition using the acetal and the orthoester as dienophiles or using s-triazine derivative as a Schiff base is also described. The electrocyclic reaction of the Schiff base was also examined to synthesize the quinoline compound.