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The Catalytic Enantioselective Total Synthesis of (+)-Liphagal

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. PMCID PMC3361906. https://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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/anie.201101842DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/anie.201101842/abstractPublisherArticle
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3361906/PubMed CentralArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
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.
Funders:
Funding AgencyGrant Number
King Abdullah University of Science and Technology (KAUST)KUS-11- 006-02
NIHR01M080269-01
Gordon and Betty Moore FoundationUNSPECIFIED
AbbottUNSPECIFIED
AmgenUNSPECIFIED
Boehringer IngelheimUNSPECIFIED
CaltechUNSPECIFIED
Eli LillyUNSPECIFIED
Danish Technical UniversityUNSPECIFIED
Jorcks foundationUNSPECIFIED
Otto Mønsteds FoundationUNSPECIFIED
AmGen Scholars ProgramUNSPECIFIED
Subject Keywords:arynes; asymmetric catalysis; natural products; terpenoids; total synthesis
Issue or Number:30
PubMed Central ID:PMC3361906
Record Number:CaltechAUTHORS:20110622-115436125
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20110622-115436125
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:03 Oct 2019 02:53

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