title: Photooxygenation of Furylalkylamines: Easy Access to Pyrrolizidine and Indolizidine Scaffolds.
abstract: A highly adaptable method targeting the ubiquitous and very important pyrrolizidine and indolizidine scaffolds is presented. The general synthetic utility of the method is underscored by its application to the rapid and easy synthesis of five natural products starting from readily accessible alkylfuran precursors. These unprotected primary furylalkylamines are subjected to photooxygenation conditions, which initiate a complex cascade reaction sequence concluding with the production of high value motifs. This sequence can be tailored to need by varying the choice of both photosensitizer and base additive.
authors.affiliation: Department of Chemistry, University of Crete, Vasilika Vouton, 71003, Iraklion, Crete, Greece.
authors.forename: Dimitris
authors.initials: D
authors.lastname: Kalaitzakis
authors.affiliation: Department of Chemistry, University of Crete, Vasilika Vouton, 71003, Iraklion, Crete, Greece.
authors.forename: Myron
authors.initials: M
authors.lastname: Triantafyllakis
authors.affiliation: Department of Chemistry, University of Crete, Vasilika Vouton, 71003, Iraklion, Crete, Greece.
authors.forename: Manolis
authors.initials: M
authors.lastname: Sofiadis
authors.affiliation: Department of Chemistry, University of Crete, Vasilika Vouton, 71003, Iraklion, Crete, Greece.
authors.forename: Dimitris
authors.initials: D
authors.lastname: Noutsias
authors.affiliation: Department of Chemistry, University of Crete, Vasilika Vouton, 71003, Iraklion, Crete, Greece. vasil@chemistry.uoc.gr.
authors.forename: Georgios
authors.initials: G
authors.lastname: Vassilikogiannakis
mesh_terms: D000588:Amines / Q000737:chemistry*; D054836:Indolizidines / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D055668:Photochemical Processes; D011763:Pyrrolizidine Alkaloids / Q000737:chemistry*
chemical_list: D000588:Amines; D054836:Indolizidines; D011763:Pyrrolizidine Alkaloids; D010100:Oxygen
keywords: alkaloids; indolizidines; pandalizines; pyrrolizidines; singlet oxygen