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.
Synthesis of Azaphilones and Related Molecules by Employing Cycloisomerization of o-Alkynylbenzaldehydes†
Article first published online: 25 FEB 2004
Copyright © 2004 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 43, Issue 10, pages 1239–1243, February 27, 2004
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
- Issue published online: 25 FEB 2004
- Article first published online: 25 FEB 2004
- Manuscript Received: 8 OCT 2003
- 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.