4.6 Article

Access to Indole-Fused Benzannulated Medium-Sized Rings through a Gold(I)-Catalyzed Cascade Cyclization of Azido-Alkynes

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 51, Pages 12992-12997

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202101824

Keywords

alpha-imino gold(I) carbenes; arylation; gold catalysis; heterocycles; medium-sized rings

Funding

  1. JSPS KAKENHI [17H03971, 20K06938]
  2. AMED [JP20am0101092j, JP20gm1010007]
  3. Tokyo Biochemical Research Foundation (TBRF)
  4. Grants-in-Aid for Scientific Research [20K06938, 17H03971] Funding Source: KAKEN

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This study demonstrates the successful synthesis of benzannulated indole-fused medium-sized tetracycles through alpha-imino gold carbene chemistry, providing a new approach to explore bioactive compounds.
Because benzannulated and indole-fused medium-sized rings are found in many bioactive compounds, combining these fragments might lead to unexplored areas of biologically relevant and uncovered chemical space. Herein is shown that alpha-imino gold carbene chemistry can play an important role in solving the difficulty in the formation of medium-sized rings. Namely, phenylene-tethered azido-alkynes undergo arylative cyclization through the formation of a gold carbene intermediate to afford benzannulated indole-fused medium-sized tetracycles. The reactions allow a range of different aryl substitution patterns and efficient access to these otherwise difficult-to-obtain medium-sized rings. This study also demonstrates the feasibility of the semihollow-shaped C-dtbm ligand for the construction of a nine-membered ring.

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