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.
Instituto Universitario de Química Organometálica "Enrique Moles", Unidad asociada al C.S.I.C., Universidad de Oviedo, 33071 Oviedo, Spain. barluenga@uniovi.es
José
J
Barluenga
Carlos
C
Mateos
Fernando
F
Aznar
Carlos
C
Valdés
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