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Titanium catalyzed [2σ + 2π] cycloaddition of bicyclo[1.1.0]-butanes with 1,3-dienes for efficient synthesis of stilbene bioisosteres

Yonghong Liu, Zhixian Wu, Jing-Ran Shan (), Huaipu Yan, Er-Jun Hao () and Lei Shi ()
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Yonghong Liu: Cancer Hospital of Dalian University of Technology
Zhixian Wu: Cancer Hospital of Dalian University of Technology
Jing-Ran Shan: University of California Los Angeles
Huaipu Yan: Dalian University of Technology
Er-Jun Hao: Henan Normal University
Lei Shi: Cancer Hospital of Dalian University of Technology

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: Abstract Natural stilbenes have shown significant potential in the prevention and treatment of diseases due to their diverse pharmacological activities. Here we present a mild and effective Ti-catalyzed intermolecular radical-relay [2σ + 2π] cycloaddition of bicyclo[1.1.0]-butanes and 1,3-dienes. This transformation enables the synthesis of bicyclo[2.1.1]hexane (BCH) scaffolds containing aryl vinyl groups with excellent regio- and trans-selectivity and broad functional group tolerance, thus offering rapid access to structurally diverse stilbene bioisosteres.

Date: 2024
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DOI: 10.1038/s41467-024-48494-9

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