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Paper | Special issue | Vol 47, No. 1, 1998, pp.205-219
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)6
Synthesis of Vinca Alkaloids and Related Compounds, Part LXXXIX. Some Unexpected Reactions of Compounds Containing the D-Seco-aspidospermane Ring System

György Kalaus, Imre Juhász, Kinga Steinhauser, István Greiner, Mária Kajtár-Peredy, János Brlik, Lajos Szabó, and Csaba Szántay*

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


Interaction of the tryptamine derivative (3) with the formyl ester (4) gave (±)-20-deethyl-2,16-didehydro-14,16-bis(methoxycarbonyl)-3-phenyl-3,14-seco-20-epiaspidospermidine (7) instead of the expected acetal (6). The product of the reaction of 3 with the acetoacetic aldehyde derivative (5) was ethylene acetal of (±)-2,16-didehydro-16-methoxycarbonyl-3-phenyl-14,15-dinoraspidospermidin-19-one (8), it was readily convertible into the reactive intermediate (10). Further build-up starting from secondary amine (11) gave the N(4)-substituted derivatives, while 10 afforded products with unexpected structures. The reaction of 10 with acetic anhydride yielded different products depending on the reaction conditions.