1.
J Org Chem
; 80(20): 10119-26, 2015 Oct 16.
Artículo
en Inglés
| MEDLINE
| ID: mdl-26366609
RESUMEN
An original and efficient synthesis of quinolizidinones through a one-pot two-component cascade reaction of norlobelanine with in situ generated ketenes is reported. Functionalized fused azabicyclic scaffolds bearing multiple stereogenic centers were prepared with excellent diastereoselectivities. Mild optimized conditions involving a key "shuttle base" deprotonation strategy was applied to the synthesis, in a short sequence, of a constrained mimetic of the privileged H-bonded conformation of (-)-lobeline.