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Communication | Special issue | Vol 72, No. 1, 2007, pp.175-179
Published online, 23rd January, 2007
DOI: 10.3987/COM-06-S(K)43
Diastereoselective Construction of Indolo[2,3-a]quinolizidine Skeleton by Cycloaddition Reaction of 3,4-Dihydro-β-carbolines with γ,δ-Unsaturated β-Ketoesters

Kazuhiro Nagata, Yusuke Sekishiro, and Takashi Itoh*

*School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan

Abstract

Cycloaddition reaction of 3,4-dihydro-β-carboline derivatives with γ,δ-unsaturated-β-ketoesters afforded octahydroindolo[2,3-a]quinolizidines in one step. The reaction was applied to the synthesis of a potential precursor of Eburnamine-Vincamine alkaloids in a highly diastereoselective manner.