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Published August 11, 2004 | Supplemental Material
Journal Article Open

The Total Synthesis of (+)-Dragmacidin F


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.

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Supplemental Material - ja046695bsi20040704_022411_si.pdf


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