Abstract
In our continuing study of the reactivity and synthetic application of indolylborate as a versatile synthetic intermediate, we found that the use of indolylborate in palladium-catalyzed cross -coupling reaction is highly effective for the synthesis of indole derivatives. The present account deals with the results concerning a novel approach to indole alkaloids based on the use of the palladium-catalyzed cross-coupling. Dimeric indole alkaloid, yuechuke, was synthesized through the palladium-catalyzed carbonylative cross-coupling reaction. Pyridocarbazole alkaloids (ellip-ticine, olivacine, and their related alkaloids), and indolophenanthridine alkaloid (calothrixins A and B) were obtained by the use of cyclization/cross-coupling domino reaction. In addition, (CuOTf) 2 toluene complex was demonstrated to catalyze 6π-electrocyclization of hexatrienes, leading to pyrido [4,3-b] carbazoles.
| Original language | English |
|---|---|
| Pages (from-to) | 117-129 |
| Number of pages | 13 |
| Journal | Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry |
| Volume | 74 |
| Issue number | 2 |
| DOIs | |
| Publication status | Published - 2016 |
| Externally published | Yes |
Keywords
- Carbonylative cross - Coupling reaction
- Copper-catalyzed 6π-electrocyclization
- Cyclization/cross-coupling domino reaction
- Indole alkaloids
- Indolylborate
ASJC Scopus subject areas
- Organic Chemistry