Day, Joshua J. and McFadden, Ryan M. and Virgil, Scott C. and Kolding, Helene and Alleva, Jennifer L. and Stoltz, Brian M. (2011) The Catalytic Enantioselective Total Synthesis of (+)-Liphagal. Angewandte Chemie International Edition, 50 (30). pp. 6814-6818. ISSN 1433-7851 http://resolver.caltech.edu/CaltechAUTHORS:20110622-115436125
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Abstract
Ring a ding: The meroterpenoid natural product (+)-liphagal has been synthesized enantioselectively in 19 steps from commercially available materials. The trans-homodecalin system was achieved by ring expansion followed by stereoselective hydrogenation.
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| Additional Information: | © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: March 15, 2011; Article first published online: 10 June 2011. This publication is based on work supported by Award No. KUS-11-006-02, made by the King Abdullah University of Science and Technology (KAUST). We wish to thank the NIH-NIGMS (R01M080269-01), the Gordon and Betty Moore Foundation, Abbott, Amgen, Boehringer Ingelheim, and Caltech for generous funding. R.M.M. thanks Eli Lilly for a graduate fellowship. H.K. acknowledges the travelling scholarship of the Danish Technical University, the Jorcks foundation, and the Otto Mønsteds foundation for financial support. J.L.A. gratefully acknowledges the Amgen Foundation for funding through the Amgen Scholars program. We thank Prof. E. N. Jacobsen and Dr. S. J. Zuend for a kind donation of both (R)-t-leucine and their optimal Strecker catalyst. | ||||||||||||||||||||||||||
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| Subject Keywords: | arynes; asymmetric catalysis; natural products; terpenoids; total synthesis | ||||||||||||||||||||||||||
| Record Number: | CaltechAUTHORS:20110622-115436125 | ||||||||||||||||||||||||||
| Persistent URL: | http://resolver.caltech.edu/CaltechAUTHORS:20110622-115436125 | ||||||||||||||||||||||||||
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| Official Citation: | Day, J. J., McFadden, R. M., Virgil, S. C., Kolding, H., Alleva, J. L. and Stoltz, B. M. (2011), The Catalytic Enantioselective Total Synthesis of (+)-Liphagal. Angewandte Chemie International Edition, 50: 6814–6818. doi: 10.1002/anie.201101842 | ||||||||||||||||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||||||||||||||||
| ID Code: | 24168 | ||||||||||||||||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||||||||||||||||
| Deposited By: | Jason Perez | ||||||||||||||||||||||||||
| Deposited On: | 19 Jul 2011 17:01 | ||||||||||||||||||||||||||
| Last Modified: | 19 Jul 2011 17:01 |
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