Published August 11, 2004
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Journal Article
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The Total Synthesis of (+)-Dragmacidin F
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.
Additional Information
© 2004 American Chemical Society. Received June 4, 2004; Publication Date (Web): July 20, 2004. 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.Attached Files
Supplemental Material - ja046695bsi20040704_022411_si.pdf
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ja046695bsi20040704_022411_si.pdf
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Additional details
- Eprint ID
- 74344
- Resolver ID
- CaltechAUTHORS:20170215-153256032
- R01GM65961-01
- NIH
- National Defense Science and Engineering Graduate (NDSEG) Fellowship
- Eli Lilly
- Created
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2017-02-16Created from EPrint's datestamp field
- Updated
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2021-11-11Created from EPrint's last_modified field