Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 51, Pages 12992-12997Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202101824
Keywords
alpha-imino gold(I) carbenes; arylation; gold catalysis; heterocycles; medium-sized rings
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Funding
- JSPS KAKENHI [17H03971, 20K06938]
- AMED [JP20am0101092j, JP20gm1010007]
- Tokyo Biochemical Research Foundation (TBRF)
- 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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