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. 2024 Feb 21;30(11):e202302963.
doi: 10.1002/chem.202302963. Epub 2024 Jan 8.

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

Keisuke Tokushige  1 , Takumi Abe  1
Affiliations
Free article

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

Keisuke Tokushige et al. Chemistry. .
Free article

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.

Keywords: C3−N1’ bisindoles; alkaloid; bromination; rivularin A; umpolung.

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