title: Regioselective Synthesis of Isoquino[1,2-b][3]benzazepines (Homoprotoberberines) through 11-Membered-Ring Stilbene Lactams Obtained by Radical Macrocyclization.
abstract: Silylated 11-membered-ring stilbene lactams 3 (E and Z) were easily prepared by intramolecular addition of an aryl radical to a trimethylsilylacetylene. Oxidation of their hindered stilbene double bonds with dioxiranes gave oxidative cleavage of their electron-rich aromatic rings. However, reduction of the amide to an amine functionality in both lactams (E and Z) triggers a regioselective [7,6]-transannular cyclization to isoquino[1,2-b][3]benzazepines (homoprotoberberines).
authors.affiliation: Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany.
authors.forename: Gema
authors.initials: G
authors.lastname: Rodríguez
authors.forename: Luis
authors.initials: L
authors.lastname: Castedo
authors.forename: Domingo
authors.initials: D
authors.lastname: Domínguez
authors.forename: Carlos
authors.initials: C
authors.lastname: Saá
authors.forename: Waldemar
authors.initials: W
authors.lastname: Adam