Abstract
2,2′-Biindolyl natural products have a long history of applications owing to their
unique structural features and biological activities. In this Account, we describe
the recent progress achieved by our research group in the total syntheses of several
2,2′-biindolyl natural products using the cyanide-catalyzed imino-Stetter reaction
as the key reaction to construct the 2,2′-biindolyl scaffold from 2-aminocinnamic
acid derivatives and indole-2-carboxaldehydes. The development of a novel protocol
to access 2,2′-bisindole-3-acetic acid derivatives via the cyanide-catalyzed imino-Stetter
reaction and its application to the total syntheses of class I (arcyriaflavin A),
class II (iheyamines A and B), and class III (calothrixin B) 2,2′-biindolyl natural
products are discussed.
1. Introduction
2. Synthesis of 2,2′-Biindolyl Compounds via Cyanide-Catalyzed Imino-Stetter Reaction
3. Total Synthesis of Arcyriaflavin A
4. Total Syntheses of Iheyamines A and B
5. Total Synthesis of Calothrixin B
6. Conclusion
Key words
2,2′-biindolyl alkaloids - cyanide catalyst - imino-Stetter reaction - structural
diversity - total synthesis
