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An attempt to construct an indole-fused azabicyclo3.3.1nonane framework via radical cyclization

Singh, VK and Ghosh, U and Chakraborty, TK (2023) An attempt to construct an indole-fused azabicyclo3.3.1nonane framework via radical cyclization. In: Organic and Biomolecular Chemistry, 21 (17). pp. 3697-3701.

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Official URL: https://doi.org/10.1039/D3OB00479A


The structural motif of an indole-fused azabicyclo3.3.1nonane is common in many biologically significant indole-based natural products. Because of its structural complexity, this N-bridged scaffold has become an enticing target for organic chemists. Many efficient strategies have been developed to access this ring system synthetically, but a radical approach remains unexplored. Herein, we report a radical-based strategy to construct an indole-fused azabicyclo3.3.1nonane structural framework. Although our initial attempt to use a Cp2TiCl-mediated radical cyclization method was found to be unsuccessful, an alternative approach using a SmI2-mediated radical cyclization protocol was effective for enabling the desired ring closure, leading to the target indole-fused azabicyclo3.3.1nonane ring system. The modular approach developed here can be extended with appropriate functionalities on this indole-fused N-bridged ring system to synthesize many alkaloids.

Item Type: Journal Article
Publication: Organic and Biomolecular Chemistry
Publisher: Royal Society of Chemistry
Additional Information: The copyright of this article belongs to Royal Society of Chemistry.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 14 Jun 2023 10:59
Last Modified: 14 Jun 2023 10:59
URI: https://eprints.iisc.ac.in/id/eprint/81886

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