Synthesis of Strained γ‐Lactams by Palladium(0)‐Catalyzed C(sp3)−H Alkenylation and Application to Alkaloid Synthesis. Issue 8 (22nd January 2016)

• Record Type: Journal Article
• Authors: Holstein, Philipp M.; Dailler, David; Vantourout, Julien; Shaya, Janah; Millet, Anthony; Baudoin, Olivier
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 8(2016)
• Page Start: 2805
• Page End: 2809
• Publication Date: 2016-01-22
• Subjects: C−C coupling -- C−H activation -- natural products -- nitrogen heterocycles -- palladium; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201511457
• Languages: English
• ISSNs: 1433-7851

Abstract

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. Abstract : Strain away : A variety of strained α‐alkylidene‐γ‐lactams were synthesized 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.