On Demand Synthesis of C3−N1’ Bisindoles by a Formal Umpolung Strategy: First Total Synthesis of (±)‐Rivularin A
Keisuke Tokushige, Takumi Abe
Abstract
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.
Topics & Concepts
UmpolungIndolineIndole testRing (chemistry)Formal synthesisTotal synthesisChemistryCombinatorial chemistryStereochemistryOrganic chemistryCatalysisNucleophileChemical synthesis and alkaloidsMarine Sponges and Natural ProductsAlkaloids: synthesis and pharmacology