195299-16-2

Upstream product

• 195299-15-1 2-cyano-5-oxazolopyrrolidine 
• 2032-35-1 Bromoacetaldehyde diethyl acetal 

Downstream Products

• 195299-21-9 1-[(1S,2R,3R,5R)-8-((R)-2-Hydroxy-1-phenyl-ethyl)-3-methoxy-8-aza-bicyclo[3.2.1]oct-2-yl]-ethanone 
• 195299-20-8 1-[(1S,5R)-3-Chloro-8-((R)-2-hydroxy-1-phenyl-ethyl)-8-aza-bicyclo[3.2.1]oct-2-yl]-ethanone 
• 195299-18-4 (E)-5-((3R,5R,7aS)-3-Phenyl-hexahydro-pyrrolo[2,1-b]oxazol-5-yl)-pent-3-en-2-one 
• 195299-17-3 (3R,5R,7aS)-5-(2,2-Diethoxy-ethyl)-3-phenyl-hexahydro-pyrrolo[2,1-b]oxazole 
• 178625-94-0 2-[2-(2,2-diethoxyethyl)pyrrolidin-1-yl]-2-phenylethanol 

Relevant 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

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.