On Demand Synthesis of C3-N1' Bisindoles by a Formal Umpolung Strategy: First Total Synthesis of ()-Rivularin A

In this work, a straightforward synthesis of C3-N1' bisindolines is achieved by a formal umpolung strategy. The protocols were tolerant of a wide variety of substituents on the indole and indoline ring. In addition, the C3-N1' bisindolines could be converted to C3-N1' indole-indolines and C3-N1'-bisindoles. Also, we have successfully synthesized (+/-)-rivularin A through a biomimetic late-stage tribromination as a key step. On Demand Synthesis of C3-N1' Bisindoles!!: Unified synthesis of C3-N1' bisindolines, indole/indolines, and bisindoles was accomplished by a formal umpolung strategy. Good functional group tolerance enabled the first total synthesis of polybrominated C3-N1' bisindole alkaloid rivularin A.image