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Synthesis of Strained γ‐Lactams by Palladium(0)‐Catalyzed C(sp3)−H Alkenylation and Application to Alkaloid Synthesis |
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| Authors: | Dr. Philipp M. Holstein David Dailler Julien Vantourout Janah Shaya Dr. Anthony Millet Prof. Dr. Olivier Baudoin |
| Affiliation: | 1. Université Claude Bernard Lyon 1, CNRS UMR 5246, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, CPE Lyon, Villeurbanne, France;2. University of Basel, Department of Chemistry, Basel, Switzerland |
| Abstract: | A variety of strained α‐alkylidene‐γ‐lactams were synthesized by palladium(0)‐catalyzed intramolecular C(sp3)?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. |
| Keywords: | C− C coupling C− H activation natural products nitrogen heterocycles palladium |