title: Synthesis and chemical diversity analysis of bicyclo[3.3.1]non-3-en-2-ones.
abstract: Functionalized bicyclo[3.3.1]non-3-en-2-ones are obtained from commercially available phenols by a hypervalent iodine oxidation, enone epoxidation, epoxide thiolysis, and intramolecular aldol reaction sequence. Reaction optimization studies identified room temperature as well as microwave-mediated procedures, providing moderate to good yields (57%-88%) in the thiophenol-mediated epoxide opening and intramolecular aldol reaction. In addition, the isolation of a key intermediate and in situ NMR studies supported the mechanistic hypothesis. The bicyclic ring products occupy novel chemical space according to ChemGPS and Chemaxon chemical diversity and cheminformatics analyses.
authors.affiliation: Center for Chemical Methodologies and Library Development, University of Pittsburgh, Pittsburgh, PA 15260, USA.
authors.forename: Jared T
authors.initials: JT
authors.lastname: Hammill
authors.forename: Julia
authors.initials: J
authors.lastname: Contreras-García
authors.forename: Aaron M
authors.initials: AM
authors.lastname: Virshup
authors.forename: David
authors.initials: D
authors.lastname: Beratan
authors.forename: Weitao
authors.initials: W
authors.lastname: Yang
authors.forename: Peter
authors.initials: P
authors.lastname: Wipf
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