Synlett 2014; 25(09): 1263-1266
DOI: 10.1055/s-0033-1341081
letter
© Georg Thieme Verlag Stuttgart · New York

Serendipitous Discovery of a Cascade Approach to Perhydrodibenzofuranones Related to the Natural Product Incarviditone

Authors

  • Stephania Christou

    a   School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK   Fax: +44(161)2754598   Email: roger.whitehead@manchester.ac.uk
  • Alyn C. Edwards

    a   School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK   Fax: +44(161)2754598   Email: roger.whitehead@manchester.ac.uk
  • Robin G. Pritchard

    a   School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK   Fax: +44(161)2754598   Email: roger.whitehead@manchester.ac.uk
  • Peter Quayle

    a   School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK   Fax: +44(161)2754598   Email: roger.whitehead@manchester.ac.uk
  • Ian J. Stratford

    b   Manchester Pharmacy School, University of Manchester, Oxford Road, Manchester, M13 9PL, UK
  • Roger C. Whitehead*

    a   School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK   Fax: +44(161)2754598   Email: roger.whitehead@manchester.ac.uk
Further Information

Publication History

Received: 17 February 2014

Accepted after revision: 07 March 2014

Publication Date:
03 April 2014 (online)


Graphical Abstract

Abstract

The unexpected discovery of an eliminative deprotection and cyclodimerization cascade reaction sequence led to the preparation of a series of perhydrodibenzofuranones that bear a structural resemblance to the natural product incarviditone. One of the novel dimers was found to show significant antiproliferative activity towards a non-small-cell lung cancer cell line, and represents a useful lead compound for the discovery of more potent anti-cancer agents.

Supporting Information