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The Total Syntheses of Basiliolide C, epi-Basiliolide C, and Protecting-Group-Free Total Syntheses of Transtaganolides C and D

Gordon, Jonny R. and Nelson, Hosea M. and Virgil, Scott C. and Stoltz, Brian M. (2014) The Total Syntheses of Basiliolide C, epi-Basiliolide C, and Protecting-Group-Free Total Syntheses of Transtaganolides C and D. Journal of Organic Chemistry, 79 (20). pp. 9740-9747. ISSN 0022-3263. https://resolver.caltech.edu/CaltechAUTHORS:20141015-093052860

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Abstract

The total syntheses of basiliolide C and previously unreported epi-basiliolide C are achieved by an Ireland–Claisen/Diels–Alder cascade. The development of a palladium catalyzed cross-coupling of methoxy alkynyl zinc reagents allows for the protecting-group-free syntheses of transtaganolides C and D. Syntheses of transtaganolides C and D are accomplished in a single operation to generate three rings, two all-carbon quaternary centers, and four tertiary stereocenters from a monocyclic, achiral precursor.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/jo501924uDOIArticle
http://pubs.acs.org/doi/abs/10.1021/jo501924uPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/jo501924uPublisherSupporting Information
ORCID:
AuthorORCID
Nelson, Hosea M.0000-0002-4666-2793
Virgil, Scott C.0000-0001-8586-5641
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2014 American Chemical Society. Received: August 19, 2014. Publication Date (Web): September 22, 2014. The authors wish to thank the NSF (Award 1265591), Amgen, the Gordon and Betty Moore Foundation, and Caltech for financial support. J.R.G. thanks the Rose Hill Foundation for a predoctoral fellowship. H.M.N. thanks the NSF and Ford Foundation for predoctoral fellowships. Prof. Giovanni Appendino and Prof. Eduardo Muñoz are acknowledged for the biological testing of synthetically derived transtaganolide C. Dr. Kei Murakami is acknowledged for his contribution to the preparation of racemic transtaganolides C and D. Dr. Alexander F. G. Goldberg and Mr. Robert A. Craig II are acknowledged for useful discussions regarding synthetic strategies. Ms. Katerina M. Korch and Mr. Corey M. Reeves are acknowledged for assistance in manuscript preparation. Dr. David Vander-Velde is acknowledged for NMR assistance.
Funders:
Funding AgencyGrant Number
NSFCHE-1265591
AmgenUNSPECIFIED
Gordon and Betty Moore FoundationUNSPECIFIED
CaltechUNSPECIFIED
Rose Hill FoundationUNSPECIFIED
NSF Predoctoral FellowshipUNSPECIFIED
Ford FoundationUNSPECIFIED
Issue or Number:20
Record Number:CaltechAUTHORS:20141015-093052860
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20141015-093052860
Official Citation:The Total Syntheses of Basiliolide C, epi-Basiliolide C, and Protecting-Group-Free Total Syntheses of Transtaganolides C and D Jonny R. Gordon, Hosea M. Nelson, Scott C. Virgil, and Brian M. Stoltz The Journal of Organic Chemistry 2014 79 (20), 9740-9747
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:50396
Collection:CaltechAUTHORS
Deposited By: Jason Perez
Deposited On:15 Oct 2014 21:01
Last Modified:09 Mar 2020 13:19

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