Advertisement

Total Synthesis of the Ubiquitin-Activating Enzyme Inhibitor (+)-Panepophenanthrin

Authors

  • Xiaoguang Lei,

    1. Department of Chemistry and, Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1) 617-353-6466
    Search for more papers by this author
  • Richard P. Johnson Prof. Dr.,

    1. Department of Chemistry, University of New Hampshire, Durham, NH 03824, USA
    Search for more papers by this author
  • John A. Porco Jr. Prof. Dr.

    1. Department of Chemistry and, Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA, Fax: (+1) 617-353-6466
    Search for more papers by this author

  • We thank Chaomin Li for helpful discussions, Dr. Ryuichi Sekizawa (Showa Pharmaceutical University) for providing authentic panepophenanthrin, and Dr. Emil Lobkovsky (Cornell University) for X-ray crystal structure analysis. Financial support from the American Cancer Society (RSG-01-135-01, J.A.P, Jr.) and the NIH (P50 GM067041) is gratefully acknowledged. R.P.J. acknowledges the Norman and Anna S. Waite Professorship for support.

Abstract

original image

The [4+2] dimerization of epoxyquinol 1 is rendered irreversible by formation of a hemiacetal in the enantioselective total synthesis of the ubiquitin-activating enzyme inhibitor (+)-panepophenanthrin (2).

Ancillary