Financial support was provided by a Grant-in-Aid for Young Scientists (S) and Scientific Research (S) from JSPS. Y.S. and H.U. thank the JSPS for research fellowships.
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Catalytic Asymmetric Total Synthesis of ent-Hyperforin†
Article first published online: 8 JAN 2010
DOI: 10.1002/anie.200906678
Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Shimizu, Y., Shi, S.-L., Usuda, H., Kanai, M. and Shibasaki, M. (2010), Catalytic Asymmetric Total Synthesis of ent-Hyperforin. Angewandte Chemie International Edition, 49: 1103–1106. doi: 10.1002/anie.200906678
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Publication History
- Issue published online: 26 JAN 2010
- Article first published online: 8 JAN 2010
- Manuscript Received: 26 NOV 2009
Funded by
- JSPS
Keywords:
- asymmetric synthesis;
- Claisen rearrangement;
- homogeneous catalysis;
- natural products;
- rearrangement
Graphical Abstract
Key to success: The first catalytic asymmetric total synthesis of ent-hyperforin (see picture) was accomplished by using a Diels–Alder reaction promoted by a chiral cationic iron catalyst (A; 96 % ee, d.r.>33:1), a diastereoselective Claisen rearrangement (B; 12:1 selectivity), an intramolecular aldol reaction (C), and a vinylogous Pummerer rearrangement (D) as key steps.