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Communication | Regular issue | Vol 27, No. 3, 1988, pp.657-661
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4429
Ion-radical promoted Cyclization of a δ,ε-Vinylimine: The Total Synthesis of (±)-Tuboxenine

Dominique Cartier, Mohammed Ouahrani, Georgette Hugel, and Jean Lévy

*Laboratorie de Pharmacognosie, Facluté de Pharmacie, U.A. n°492 au C.N.R.S., 51, rue Cognacq-Jay, F-51096 Reims Cedex, France


3-Oxo-1,2,18,19-tetradehydroaspidospermidine 8b was synthesized by a modification of a previous synthesis of vincadifformine 10. It was cyclized (Na/THF) to 3-oxotuboxenine 22, which was reduced with LiAIH4 to (±)-tuboxenine 1.