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Paper | Regular issue | Vol 55, No. 5, 2001, pp.873-880
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9146
Synthesis of Vinca Alkaloids and Related Compounds 95. Attempted Build-up of the Aspidospermidine Skelton by [4+2] Cycloaddition. Some Unexpected Reactions, and Formation of a New Ring System

István Vágó, György Kalaus,* István Greiner, Mária Kajtár-Peredy, János Brlik, Lajos Szabó, and Csaba Szántay*

*Department for Organic Chemistry, Technical University of Budapset, Gellért tér 4, P.O. Box 91, H-1521 Budapset, Hungary


The reaction of the 2-vinylindole derivative (10) with methyl 4-formylbutanoate (11a) gave a pyrido[1,2-a]indole (13), instead of the expected seco-aspidospermidine (12). Similarly, this cycloaddition reaction failed with the vinyl-enamide (19), the products were two 5H-pyrido[1’,2’:1,8]azocino[5,4-b]-indole derivatives, (20 and 21).