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The Total Synthesis of (+)-Dragmacidin F

Garg, Neil K. and Caspi, Daniel D. and Stoltz, Brian M. (2004) The Total Synthesis of (+)-Dragmacidin F. Journal of the American Chemical Society, 126 (31). pp. 9552-9553. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20170420-115314385

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Abstract

The first total synthesis of (+)-dragmacidin F has been accomplished, establishing the absolute configuration of this biologically important, antiviral marine alkaloid. The convergent route described features a palladium-mediated oxidative pyrrole carbocylization reaction to construct the [3.3.1] bicycle, as well as a highly selective Suzuki coupling to build the carbon skeleton of the natural product. A late-stage Neber rearrangement allows for the facile installation of the aminoimidazole moiety to provide (+)-dragmacidin F.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja046695bDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja046695bPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja046695bPublisherSupporting Information
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2004 American Chemical Society. We are grateful to the NIH-NIGMS (R01 GM65961-01), DOD (NDSEG graduate fellowship to N.K.G.), and Eli Lilly (predoctoral fellowship to D.D.C.) for generous financial support. The Dervan lab is acknowledged for helpful discussions and the generous use of instrumentation. We also thank Drs. R. Riccio and A. Casapullo for an authentic sample of (−)-dragmacidin F.
Funders:
Funding AgencyGrant Number
NIHR01 GM65961-01
National Defense Science and Engineering Graduate (NDSEG) FellowshipUNSPECIFIED
Eli LillyUNSPECIFIED
Issue or Number:31
Record Number:CaltechAUTHORS:20170420-115314385
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170420-115314385
Official Citation:The Total Synthesis of (+)-Dragmacidin F Neil K. Garg, Daniel D. Caspi, and Brian M. Stoltz Journal of the American Chemical Society 2004 126 (31), 9552-9553 DOI: 10.1021/ja046695b
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76764
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:20 Apr 2017 20:46
Last Modified:03 Oct 2019 17:49

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