T.R.R.P. is grateful for financial support from National Institute of General Medical Sciences (64831-06) for this work and related studies on scyphostatin. We thank Taridorn Buajarern for providing 1H and 13C NMR spectral data for 1, 2, and 3 in [D6]acetone for comparative purposes. We appreciate Dr. Arkady Krasovskiy for his insightful ideas regarding epoxide opening with lanthanide halides. This project has also benefited from earlier studies of R. W. Van De Water and C. Hoarau within our group.
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Communication
Total Synthesis of TK-57-164A, Isariotin F, and Their Putative Progenitor Isariotin E†
Article first published online: 17 NOV 2009
DOI: 10.1002/anie.200904716
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Cha, Jacob Y., Huang, Y. and Pettus, Thomas R. R. (2009), Total Synthesis of TK-57-164A, Isariotin F, and Their Putative Progenitor Isariotin E. Angew. Chem. Int. Ed., 48: 9519–9521. doi: 10.1002/anie.200904716
- †
Publication History
- Issue published online: 30 NOV 2009
- Article first published online: 17 NOV 2009
- Manuscript Revised: 1 OCT 2009
- Manuscript Received: 24 AUG 2009
Funded by
- National Institute of General Medical Sciences. Grant Number: 64831-06
Keywords:
- biomimetic synthesis;
- cyclization;
- dearomatization;
- resorcinol;
- total synthesis
Keeping it simple: A simple strategy for the total synthesis of three complex natural products has been developed, while also confirming the putative generation of 1 and 2 from 3. The benefits of a simple dissymmetric 2,5-cyclohexadienone are illustrated and provide the foundation for rapid diastereoselective functionalization leading to the first total synthesis of these compounds.