Citation: Ze-Hong Zheng, Mu-Qiu Chen, Jin Zhou, Jie Wang, Yan-Rong Wei, Cheng Peng, Gu Zhan, Qian-Qian Yang, Bo Han. Diverse synthesis of bridged bicyclo[3.2.1]octa-2,6-diene and tricyclo[3.2.1.0^2,7]oct-3-ene frameworks via stepwise cascade reactions[J]. Chinese Chemical Letters, ;2025, 36(12): 111202. doi: 10.1016/j.cclet.2025.111202 shu

Diverse synthesis of bridged bicyclo[3.2.1]octa-2,6-diene and tricyclo[3.2.1.0^2,7]oct-3-ene frameworks via stepwise cascade reactions

State Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China

yangqq@cdutcm.edu.cn

hanbo@cdutcm.edu.cn

Received Date: 22 December 2024
Revised Date: 31 March 2025
Accepted Date: 11 April 2025
Available Online: 12 April 2025

Figures(5)

Strained bridged rings bicyclo[3.2.1]octane and tricyclo[3.2.1.0^2,7]octane are prevalent in natural products known for their significant biological activities. However, strategies for efficiently synthesizing these complex frameworks from simple starting materials via de novo synthesis remain underexplored. This article presents an efficient strategy that combines phosphine catalysis and photocatalysis to execute a stepwise tandem reaction involving allenoates and α-cyano cinnamaldehydes, including [3 + 2] cyclization, [5 + 2] cyclization, acyl transfer, and decarboxylation reactions, synthesizing a series of functional bicyclo[3.2.1]octa-2,6-diene and tricyclo[3.2.1.0^2,7]oct–3-ene skeleton derivatives with excellent chemoselectivity demonstrated throughout the process. Meanwhile, the reaction can also be performed via a one-pot, scalable phosphine/photocatalytic cascade process, efficiently yielding the bridged products which can serve as versatile intermediates for further applications.
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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

Diverse synthesis of bridged bicyclo[3.2.1]octa-2,6-diene and tricyclo[3.2.1.02,7]oct-3-ene frameworks via stepwise cascade reactions

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通讯作者: 陈斌, bchen63@163.com

Diverse synthesis of bridged bicyclo[3.2.1]octa-2,6-diene and tricyclo[3.2.1.0^2,7]oct-3-ene frameworks via stepwise cascade reactions