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Access to indole-fused benzannulated medium-sized rings through a gold(I)-catalyzed cascade cyclization of azido-alkynes

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 α-imino gold carbene chemistry can play an important role in solving t...

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Main Authors: Greiner, Luca C. (Author) , Inuki, Shinsuke (Author) , Arichi, Norihito (Author) , Oishi, Shinya (Author) , Suzuki, Rikito (Author) , Iwai, Tomohiro (Author) , Sawamura, Masaya (Author) , Hashmi, A. Stephen K. (Author) , Ohno, Hiroaki (Author)
Format: Article (Journal)
Language:English
Published: 10 June 2021
In: Chemistry - a European journal
Year: 2021, Volume: 27, Issue: 51, Pages: 12992-12997
ISSN:1521-3765
DOI:10.1002/chem.202101824
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chem.202101824
Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.202101824
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Author Notes:Luca C. Greiner, Shinsuke Inuki, Norihito Arichi, Shinya Oishi, Rikito Suzuki, Tomohiro Iwai, Masaya Sawamura, A. Stephen K. Hashmi, and Hiroaki Ohno
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Summary: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 α-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.
Item Description:Gesehen am 03.05.2022
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.202101824

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