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.
Garg
Neil K
NK
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
Caspi
Daniel D
DD
Stoltz
Brian M
BM
D000818:Animals; D019380:Anti-HIV Agents / Q000138:chemical synthesis; D000998:Antiviral Agents / Q000138:chemical synthesis; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000494:pharmacology; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
D019380:Anti-HIV Agents; D000998:Antiviral Agents; D026121:Indole Alkaloids; C492392:dragmacidin F