A straightforward and versatile synthetic approach to 1-azabicyclic alkaloids.
A very straightforward route to 1-azabicyclo alkaloid scaffolds with several ring sizes is reported. The final bicyclic structures were built through a synthetic scheme that involved (i) the construction of dienic 4-piperidone systems by an imino-Diels-Alder reaction between aminotrienes and N-omega-vinylimines, in the presence of Yb(OTf)(3), and (ii) the ring-closing metathesis reaction of these cyclic dienes, under the influence of the first-generation Grubbs' Ru-complex catalyst. During this investigations, various polysubstituted azabicyclic ring skeletons, including several examples of the quinolizidine alkaloids, are reported, and their relative stereochemistry is adequately discussed.
Barluenga
José
J
Instituto Universitario de Química Organometálica "Enrique Moles", Unidad asociada al C.S.I.C., Universidad de Oviedo, 33071 Oviedo, Spain. barluenga@uniovi.es
Mateos
Carlos
C
Aznar
Fernando
F
Valdés
Carlos
C
D000470:Alkaloids / Q000138:chemical synthesis*; D001372:Aza Compounds / Q000138:chemical synthesis*; D003500:Cyclization; D007212:Indolizines / Q000138:chemical synthesis*; D008968:Molecular Conformation; D015394:Molecular Structure; D011807:Quinolizines / Q000138:chemical synthesis*
D000470:Alkaloids; D001372:Aza Compounds; D007212:Indolizines; D011807:Quinolizines