title: Asymmetric total synthesis of (+)-virosine A via sequential nucleophilic cyclizations onto an activated formamide.
abstract: The first synthesis of tetracyclic alkaloid virosine A is reported. The natural alkaloid was prepared in only 13 steps, in an enantioenriched form. The azabicyclo[2.2.2]octane core was efficiently assembled using a key Vilsmeier-Haack and Mannich cyclizations sequence performed in one pot.
authors.affiliation: Département de Chimie, Université de Sherbrooke, 2500 boulevard Université, Sherbrooke, Québec J1K 2R1, Canada. Guillaume.Belanger@USherbrooke.ca
authors.forename: Guillaume
authors.initials: G
authors.lastname: Bélanger
authors.forename: Marianne
authors.initials: M
authors.lastname: Dupuis
authors.forename: Robin
authors.initials: R
authors.lastname: Larouche-Gauthier
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D003500:Cyclization; D019665:Euphorbiaceae / Q000737:chemistry*; D005559:Formamides / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D005559:Formamides; D006576:Heterocyclic Compounds, 4 or More Rings; C574406:virosine A; C031066:formamide