title: Concise synthesis of pyrrolidine and indolizidine alkaloids by a highly convergent three-component reaction.
abstract: The synthesis of pyrrolidine and indolizidine derivatives through radical carboazidation of alkenes with α-iodoketones, followed by reductive amination, is described. When properly substituted, further lactamization afforded pyrrolizidinones in good yield. This carboazidation/reductive amination sequence was efficiently applied to the total synthesis of three different simple alkaloids, including (±)-monomorine I.
authors.affiliation: Departement für Chemie und Biochemie, University of Bern, Freiestrasse 3, 3012 Bern, Switzerland.
authors.forename: Guillaume
authors.initials: G
authors.lastname: Lapointe
authors.forename: Kurt
authors.initials: K
authors.lastname: Schenk
authors.forename: Philippe
authors.initials: P
authors.lastname: Renaud
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000586:Amination; D018360:Crystallography, X-Ray; D005609:Free Radicals / Q000737:chemistry; D054836:Indolizidines / Q000138:chemical synthesis / Q000737:chemistry*; D007212:Indolizines / Q000138:chemical synthesis / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D008968:Molecular Conformation; D011759:Pyrrolidines / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D005609:Free Radicals; D054836:Indolizidines; D007212:Indolizines; D007659:Ketones; D011759:Pyrrolidines; C538734:monomorine; C032519:pyrrolidine