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Communication | Regular issue | Vol 36, No. 3, 1993, pp.435-440
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6241
Synthesis of Functionalized Indolizino[8,7-b]indoles via 1,3-Dipolar Cycloaddition Reactions of 3,4-Dihydro-β-carboline Azomethine Ylides with Olefinic Derivatives

Guillaume Poissonnet, Marie-Héléne Théret, and Robert H. Dodd*

*Institut des Chimie des Substances Naturelles, C.N.R.S., Avenue de la Terrasse, Bat. 27, 91198 Gif-sur-Yvette Cedex, France


The 1,3-dipolar cycloaddition reaction of 3,4-dihydro-β-carboline azomethine ylide (4) with dimethyl fumarate (5) and fumaronitrile (5’) is described. The resulting hexahydroindolizine products (6) and (6’) were dehydrogenated stepwise (- H2, - 2H2, - 3H2) using KMnO4, MnO2 and DDQ as oxidants.