%0 Journal Article
%@ 0040-4020
%A Hammill, JT
%A Contreras-García, J
%A Virshup, AM
%A Beratan, DN
%A Yang, W
%A Wipf, P
%D 2010
%F pittir:22231
%J Tetrahedron
%N 31
%P 5852 - 5862
%T Synthesis and chemical diversity analysis of bicyclo[3.3.1]non-3-en-2-ones
%U http://d-scholarship-dev.library.pitt.edu/22231/
%V 66
%X 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. © 2010 Elsevier Ltd.