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The First Total Synthesis of Dragmacidin D

Garg, Neil K. and Sarpong, Richmond and Stoltz, Brian M. (2002) The First Total Synthesis of Dragmacidin D. Journal of the American Chemical Society, 124 (44). pp. 13179-13184. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20170414-143016727

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Abstract

The first total synthesis of the biologically significant bis-indole alkaloid dragmacidin D (5) has been achieved. Thermal and electronic modulation provides the key for a series of palladium-catalyzed Suzuki cross-coupling reactions that furnished the core structure of the complex guanidine- and aminoimidazole-containing dragmacidins. Following this crucial sequence, a succession of meticulously controlled final events was developed leading to the completion of the natural product.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja027822bDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja027822bPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja027822bPublisherSupporting Information
ORCID:
AuthorORCID
Sarpong, Richmond0000-0002-0028-6323
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2002 American Chemical Society. Received 23 July 2002. Published online 5 October 2002. Published in print 1 November 2002. The authors are grateful to the California Institute of Technology, the Camille and Henry Dreyfus Foundation (New Faculty Award to B.M.S.), Merck Research Laboratories, NIH-NIGMS (R01 GM65961-01), DOD (NDSEG graduate fellowship to N.K.G.), and Pfizer·UNCF (postdoctoral fellowship to R.S.) for generous financial support. The Dervan and MacMillan labs are acknowledged for helpful discussions and the generous use of instrumentation. Michael Marques, Wei Zhang, and Yen Nguyen are acknowledged for experimental assistance. We thank John Greaves (University of California, Irvine) for obtaining high-resolution mass spectra and Scott Ross of the Beckman Institute (Caltech) for assistance in obtaining NMR spectra. We gratefully acknowledge Dr. Amy E. Wright of the Harbor Branch Oceanographic Institute (North Fort Pierce, Florida) and Professor Robert J. Capon of the University of Melbourne (Parkville, Victoria, Australia) for kindly providing samples and spectra of natural dragmacidin D.
Funders:
Funding AgencyGrant Number
CaltechUNSPECIFIED
Camille and Henry Dreyfus FoundationUNSPECIFIED
Merck Research LaboratoriesUNSPECIFIED
NIHR01 GM65961-01
National Defense Science and Engineering Graduate (NDSEG) FellowshipUNSPECIFIED
Pfizer-UNCFUNSPECIFIED
Issue or Number:44
Record Number:CaltechAUTHORS:20170414-143016727
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170414-143016727
Official Citation:The First Total Synthesis of Dragmacidin D Neil K. Garg, Richmond Sarpong, and Brian M. Stoltz Journal of the American Chemical Society 2002 124 (44), 13179-13184 DOI: 10.1021/ja027822b
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76576
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:14 Apr 2017 22:32
Last Modified:03 Oct 2019 17:02

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