156472-68-3Relevant academic research and scientific papers
Concise and stereoselective syntheses of the eight natural ant defense alkaloids (+)-tetraponerine-1 to (+)-tetraponerine-8 according to the CN(R,S) strategy
Yue, Chongwei,Gauthier, Isabelle,Royer, Jacques,Husson, Henri-Philippe
, p. 4949 - 4954 (1996)
The asymmetric syntheses of all the known defense alkaloids of the ant Tetraponera sp. tetraponerines T-1 to T-8 have been accomplished in five or six steps with 20-45% overall yields. The synthesis involved in the cross-condensation of (R)-piperidin-2-ylacetaldehyde with 4-aminobutyraldehyde which upon quenching by cyanide ion gave a stable tricyclic amino nitrile 3 with both a high yield and complete diastereoselectivity. This amino nitrile is the common precursor of four tetraponerines. A similar synthesis using (R)-pyrrolidine-2-ylacetaldehyde provided the tricyclic amino nitrile 2 precursor of the four other tetraponerines.
