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Note | Regular issue | Vol 55, No. 5, 2001, pp.941-949
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9160
Diastereoselective Synthesis of 1-Aza-spiro[5.5]undecane Skeleton

Marc David, Hamid Dhimane, Corinne Vanucci-Bacqué, and Gérard Lhommet*

*Université P. et M. Curie, UMR 7611, Laboratoire de Chimie des Hétérocycles, case courrier 43, 4 Place Jussieu, F-75252 Paris Cedex 05, France


The synthesis of various bicyclic enamines (5), bearing a side chain with a multiple C-C bond or a furan ring, was performed from racemic pipecolic acid through sulfone (1c). Cyclization of these derivatives (5), via the corresponding in situ generated N-acyliminium ions, was studied in various acidic conditions to afford, in some cases, spiro intermediates (2) which possess the backbone of the histrionicotoxin family of alkaloids.