%0 Journal Article %A Garg, Neil K. %A Caspi, Daniel D. %A Stoltz, Brian M. %D 2004 %T The Total Synthesis of (+)-Dragmacidin F %U https://acs.figshare.com/articles/journal_contribution/The_Total_Synthesis_of_Dragmacidin_F/3328906 %R 10.1021/ja046695b.s001 %2 https://acs.figshare.com/ndownloader/files/5168116 %K convergent route %K dragmacidin %K pyrrole %K Neber %K carbocylization %K Suzuki %K marine alkaloid %K synthesis %K aminoimidazole moiety %K oxidative %K configuration %K installation %K Total Synthesis %K Dragmacidin %K carbon skeleton %K rearrangement %X 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. %I ACS Publications