Synthesis and chemical diversity analysis of bicyclo[3.3.1]non-3-en-2-ones

Jared T. Hammill, Julia Contreras-García, Aaron M. Virshup, David N. Beratan, Weitao Yang, Peter Wipf

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

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.

Original languageEnglish
Pages (from-to)5852-5862
Number of pages11
JournalTetrahedron
Volume66
Issue number31
DOIs
StatePublished - Jul 31 2010

Bibliographical note

Funding Information:
The authors thank Dr. Steven Geib (University of Pittsburgh) for the X-ray structure analyses of 14 and 20 , and NIH/NIGMS (P41GM081275; P50GM067082) for financial support.

Keywords

  • Bicyclo[3.3.1]nonenones
  • Chemical diversity analysis
  • Epoxyketone rearrangement
  • Ring-opening

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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