Synthesis
DOI: 10.1055/a-2343-0881
paper

RhI-Catalyzed Cycloisomerization Reactions of 1,7-Enynes To Access Cage-Like Tricyclo[3.2.2.06,8]nonenes

Jin-Bao Fan
a   Xiangya School of Pharmaceutical Sciences, Central South University, Changsha, Hunan, 410013, P. R. of China
,
Liyang Shi
b   Department of Science, Zhejiang A&F University, Hangzhou, Zhejiang, 311300, P. R. of China
,
Qing Wang
a   Xiangya School of Pharmaceutical Sciences, Central South University, Changsha, Hunan, 410013, P. R. of China
,
Yan Zeng
a   Xiangya School of Pharmaceutical Sciences, Central South University, Changsha, Hunan, 410013, P. R. of China
,
Wei Cao
a   Xiangya School of Pharmaceutical Sciences, Central South University, Changsha, Hunan, 410013, P. R. of China
,
Guangyao Zeng
a   Xiangya School of Pharmaceutical Sciences, Central South University, Changsha, Hunan, 410013, P. R. of China
,
Yingjun Zhou
a   Xiangya School of Pharmaceutical Sciences, Central South University, Changsha, Hunan, 410013, P. R. of China
,
Xu Deng
a   Xiangya School of Pharmaceutical Sciences, Central South University, Changsha, Hunan, 410013, P. R. of China
› Author Affiliations
We acknowledge the National Key Research and Development Program of China (2023YFC2606500 to X. Deng), the National Natural Science Foundation of China (22377151 to X. Deng), the Hunan Provincial Science Fund for Distinguished Young Scholars (2023JJ10083 to X. Deng), Start-up funds from Zhejiang A&F University (2019FR060 to L.-Y. Shi), and the Huxiang High-Level Talent Gathering Project from the Department of Science and Technology of Hunan Province (2022RC4029) for financial support.


Abstract

Cage-like polycycles represent a class of structurally unique and biologically promising molecules, however, efficient approaches for their synthesis are rare. Herein, we disclose RhI-catalyzed cycloisomerization reactions of 1,7-enynes containing a chelating group at the alkyne terminus, which afford unprecedented cage-like tricyclo[3.2.2.06,8]nonenes via a 7-endo-dig cyclization. This work not only provides a straightforward approach to these novel cage-like tricycles, but also unveils the under-explored π-acidic reactivity of the RhI catalyst aided by secondary chelation.

Supporting Information



Publication History

Received: 07 May 2024

Accepted after revision: 11 June 2024

Accepted Manuscript online:
11 June 2024

Article published online:
27 June 2024

© 2024. Thieme. All rights reserved

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