Stereoselective synthesis of fissoldhimine alkaloid analogues via sequential electrooxidation and heterodimerization of ureas.

Autor: Naulin E; Institut de Chimie des Substances Naturelles, CNRS, Univ. Paris-Saclay, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette, Cedex, France. geraldine.masson@cnrs.fr., Brion A; Institut de Chimie des Substances Naturelles, CNRS, Univ. Paris-Saclay, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette, Cedex, France. geraldine.masson@cnrs.fr., Biatuma D; Institut de Chimie des Substances Naturelles, CNRS, Univ. Paris-Saclay, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette, Cedex, France. geraldine.masson@cnrs.fr., Roulland E; UMR 8038, CitCom, CNRS-Université Paris Cité, Faculté de Pharmacie 4, avenue de l'Observatoire, 75006 Paris, France., Genta-Jouve G; UAR3456 CNRS LEEISA, Centre de Recherche de Montabo, IRD, 275 Route de Montabo, CEDEX BP 70620, 97334 Cayenne, France., Neuville L; Institut de Chimie des Substances Naturelles, CNRS, Univ. Paris-Saclay, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette, Cedex, France. geraldine.masson@cnrs.fr.; HitCat, Seqens-CNRS Joint Laboratory, Seqens'Lab, 78440 Porcheville, France., Masson G; Institut de Chimie des Substances Naturelles, CNRS, Univ. Paris-Saclay, 1 Avenue de la Terrasse, 91198 Gif-sur-Yvette, Cedex, France. geraldine.masson@cnrs.fr.; HitCat, Seqens-CNRS Joint Laboratory, Seqens'Lab, 78440 Porcheville, France.
Jazyk: angličtina
Zdroj: Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2024 Oct 08; Vol. 60 (81), pp. 11560-11563. Date of Electronic Publication: 2024 Oct 08.
DOI: 10.1039/d4cc02616k
Abstrakt: This study develops a biogenetic synthesis strategy using electrooxidation and heterodimerization of N -substituted pyrrolidine-1-carboxamides to create diverse analogues of the fissoldhimine alkaloid core. Under acidic conditions, 2-alkoxypyrrolidine-1-carboxamides from Shono oxidation formed endo -heterodimers with high yields and diastereoselectivity. Enantioselective heterodimerization using chiral phosphoric acid catalysis produced exo -heterodimers with high enantioselectivity.
Databáze: MEDLINE
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