title: Synthesis of Strained γ-Lactams by Palladium(0)-Catalyzed C(sp(3) )-H Alkenylation and Application to Alkaloid Synthesis.
abstract: A variety of strained α-alkylidene-γ-lactams were synthesized by palladium(0)-catalyzed intramolecular C(sp(3) )-H alkenylation from easily accessible acyclic and monocyclic bromoalkene precursors. These lactams are valuable intermediates for accessing various classes of mono- and bicylic alkaloids containing a pyrrolidine ring, as illustrated with the synthesis of an advanced model of the marine natural product plakoridine A and of the indolizidine alkaloid δ-coniceine.
authors.affiliation: Université Claude Bernard Lyon 1, CNRS UMR 5246, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, CPE Lyon, 43 Boulevard du 11 Novembre 1918, 69622, Villeurbanne, France.
authors.forename: Philipp M
authors.initials: PM
authors.lastname: Holstein
authors.affiliation: Université Claude Bernard Lyon 1, CNRS UMR 5246, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, CPE Lyon, 43 Boulevard du 11 Novembre 1918, 69622, Villeurbanne, France.|University of Basel, Department of Chemistry, St. Johanns-Ring 19, 4056, Basel, Switzerland.
authors.forename: David
authors.initials: D
authors.lastname: Dailler
authors.affiliation: Université Claude Bernard Lyon 1, CNRS UMR 5246, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, CPE Lyon, 43 Boulevard du 11 Novembre 1918, 69622, Villeurbanne, France.
authors.forename: Julien
authors.initials: J
authors.lastname: Vantourout
authors.affiliation: Université Claude Bernard Lyon 1, CNRS UMR 5246, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, CPE Lyon, 43 Boulevard du 11 Novembre 1918, 69622, Villeurbanne, France.
authors.forename: Janah
authors.initials: J
authors.lastname: Shaya
authors.affiliation: Université Claude Bernard Lyon 1, CNRS UMR 5246, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, CPE Lyon, 43 Boulevard du 11 Novembre 1918, 69622, Villeurbanne, France.
authors.forename: Anthony
authors.initials: A
authors.lastname: Millet
authors.affiliation: Université Claude Bernard Lyon 1, CNRS UMR 5246, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, CPE Lyon, 43 Boulevard du 11 Novembre 1918, 69622, Villeurbanne, France. olivier.baudoin@unibas.ch.|University of Basel, Department of Chemistry, St. Johanns-Ring 19, 4056, Basel, Switzerland. olivier.baudoin@unibas.ch.
authors.forename: Olivier
authors.identifier: http://orcid.org/0000-0002-0847-8493
authors.initials: O
authors.lastname: Baudoin
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D007769:Lactams / Q000138:chemical synthesis*; D010165:Palladium / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D000475:Alkenes; D007769:Lactams; D010165:Palladium
keywords: C−C coupling; C−H activation; natural products; nitrogen heterocycles; palladium