title: Synthesis of a library of tricyclic azepinoisoindolinones.
abstract: Hydrozirconation of 1-hexyne, the addition to in situ prepared N-acyliminium species, and ring-closing metathesis (RCM) were key steps in the preparation of a tricyclic isoindolinone scaffold. An unusual alkene isomerization process during the RCM was identified and studied in some detail. Chemical diversification for library synthesis was achieved by a subsequent alkene epoxidation and zinc-mediated aminolysis reaction. The resulting library products provided selective hits among a large number of high-throughput screens reported in PubChem, thus illustrating the utility of the novel scaffold.
authors.affiliation: Center for Chemical Methodologies & Library Development (CMLD), Department of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, PA 15260, USA.
authors.forename: Bettina
authors.initials: B
authors.lastname: Miller
authors.forename: Shuli
authors.initials: S
authors.lastname: Mao
authors.forename: Kara M George
authors.initials: KM
authors.lastname: Rosenker
authors.forename: Joshua G
authors.initials: JG
authors.lastname: Pierce
authors.forename: Peter
authors.initials: P
authors.lastname: Wipf