We thank Dr. Takafumi Kohama (Sankyo Co. LTD.) for providing 1H and 13C NMR spectra of S-15183a and Dr. Emil Lobkovsky (Cornell University) for X-ray crystal structure analysis. We thank CEM Corporation (Matthews, NC) for providing the Explorer microwave system, Bristol-Myers Squibb for an unrestricted Grant in Synthetic Organic Chemistry (J.A.P, Jr.), and Novartis Pharma AG for research support.
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Communication
Synthesis of Azaphilones and Related Molecules by Employing Cycloisomerization of o-Alkynylbenzaldehydes†
Article first published online: 25 FEB 2004
DOI: 10.1002/anie.200353037
Copyright © 2004 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Issue
Angewandte Chemie International Edition
Volume 43, Issue 10, pages 1239–1243, February 27, 2004
Additional Information
How to Cite
Zhu, J., Germain, A. R. and Porco, J. A. (2004), Synthesis of Azaphilones and Related Molecules by Employing Cycloisomerization of o-Alkynylbenzaldehydes. Angew. Chem. Int. Ed., 43: 1239–1243. doi: 10.1002/anie.200353037
- †
Publication History
- Issue published online: 25 FEB 2004
- Article first published online: 25 FEB 2004
- Manuscript Received: 8 OCT 2003
Keywords:
- alkynes;
- azaphilones;
- cycloisomerization;
- gold;
- Lewis acid catalysis
Right to the core: Gold(III)-catalyzed cycloisomerization of o-alkynylbenzaldehydes to 2-benzopyrylium salts and subsequent in situ oxidation have been employed to prepare the core structure of azaphilone natural products, such as the sphingosine kinase inhibitor S-15183 (see scheme, DCE=1,2-dichloroethane, TFA=trifluoroacetic acid)), and several unnatural azaphilones.