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.
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Communication
Total Synthesis of the Ubiquitin-Activating Enzyme Inhibitor (+)-Panepophenanthrin†
Article first published online: 22 AUG 2003
DOI: 10.1002/anie.200351862
Copyright © 2003 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Lei, X., Johnson, R. P. and Porco, J. A. (2003), Total Synthesis of the Ubiquitin-Activating Enzyme Inhibitor (+)-Panepophenanthrin. Angew. Chem. Int. Ed., 42: 3913–3917. doi: 10.1002/anie.200351862
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Publication History
- Issue published online: 22 AUG 2003
- Article first published online: 22 AUG 2003
- Manuscript Received: 12 MAY 2003
Keywords:
- cycloaddition;
- epoxyquinoids;
- natural products;
- total synthesis
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).