4.6 Article

Azido-Alkynes in Gold(I)-Catalyzed Indole Syntheses

Journal

CHEMICAL RECORD
Volume 21, Issue 12, Pages 3897-3910

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/tcr.202100202

Keywords

gold(I)-carbenes; gold-catalysis; heterocycles; natural product synthesis; medium-sized rings

Funding

  1. JSPS KAKENHI [17H03971, 20K06938]
  2. AMED [20gm1010007h0004, 20am0101092j0004]
  3. Naito Foundation
  4. Grants-in-Aid for Scientific Research [17H03971, 20K06938] Funding Source: KAKEN

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The exploitation of nitrogen-functionalized reactive intermediates plays a crucial role in the synthesis of biologically relevant scaffolds, especially those based on gold carbenes. This personal account provides a detailed explanation of the contribution to this sector by developing efficient gold-catalyzed cascade processes based on diversely functionalized azido-alkynes, with challenging cyclizations and their subsequent applications in the synthesis of pharmaceutically relevant scaffolds and natural products being key features of the research.
The exploitation of nitrogen-functionalized reactive intermediates plays an important role in the synthesis of biologically relevant scaffolds in the field of pharmaceutical sciences. Those based on gold carbenes carry a strong potential for the design of highly efficient cascade processes toward the synthesis of compounds containing a fused indole core structure. This personal account gives a detailed explanation of our contribution to this sector, and embraces the reaction development of efficient gold-catalyzed cascade processes based on diversely functionalized azido-alkynes. Challenging cyclizations and their subsequent application in the synthesis of pharmaceutically relevant scaffolds and natural products conducted in an intra- or intermolecular fashion are key features of our research.

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