title: Allenyl azide cycloaddition chemistry: application to the total synthesis of (±)-meloscine.
abstract: The pentacyclic alkaloid (±)-meloscine was prepared in 19 steps through a reaction sequence that features a putative azatrimethylenemethane intermediate, generated through cascade cyclization of an allenyl azide substrate, to deliver the core azabicyclo[3.3.0]octadiene substructure. Subsequent manipulation of the peripheral functionality then delivered (±)-meloscine.
authors.affiliation: Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA. ksf@chem.psu.edu
authors.forename: Ken S
authors.initials: KS
authors.lastname: Feldman
authors.forename: Joshua F
authors.initials: JF
authors.lastname: Antoline
mesh_terms: D001386:Azides / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis*; D011804:Quinolines / Q000138:chemical synthesis*
chemical_list: D001386:Azides; D019086:Bridged Bicyclo Compounds, Heterocyclic; D011083:Polycyclic Compounds; D011804:Quinolines; C530682:meloscine