title: Two-Component Domino Reactions Initiated from Ketenes: Serendipitous Synthesis of Quinolizidinones Analogous to Chelated Lobeline's Conformation.
abstract: 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.
authors.affiliation: Université Paris-Sud, UMR CNRS 8076 BioCIS, Université Paris-Saclay, Equipe de Chimie des Substances Naturelles , 5, rue Jean-Baptiste Clément, F-92296 Châtenay-Malabry, France.
authors.forename: Emmanuelle
authors.initials: E
authors.lastname: Drège
authors.affiliation: Université Paris-Sud, UMR CNRS 8076 BioCIS, Université Paris-Saclay, Equipe de Chimie des Substances Naturelles , 5, rue Jean-Baptiste Clément, F-92296 Châtenay-Malabry, France.
authors.forename: Pierre-Etienne
authors.initials: PE
authors.lastname: Venot
authors.affiliation: Université Paris-Sud, UMR CNRS 8076 BioCIS, Université Paris-Saclay, Equipe de Chimie des Substances Naturelles , 5, rue Jean-Baptiste Clément, F-92296 Châtenay-Malabry, France.
authors.forename: Franck
authors.initials: F
authors.lastname: Le Bideau
authors.affiliation: Institut de Chimie des Substances Naturelles, UPR CNRS 2301, Université Paris-Saclay , Bât. 27, 1, Avenue de la Terrasse, 91198 Gif-sur-Yvette cedex, France.
authors.forename: Pascal
authors.initials: P
authors.lastname: Retailleau
authors.affiliation: Université Paris-Sud, UMR CNRS 8076 BioCIS, Université Paris-Saclay, Equipe de Chimie des Substances Naturelles , 5, rue Jean-Baptiste Clément, F-92296 Châtenay-Malabry, France.
authors.forename: Delphine
authors.initials: D
authors.lastname: Joseph