Concise Report
Enantioselective Total Synthesis of (+)-Propolisbenzofuran B†
Wen-Xiu Xu,
Li-Han Zhao,
Yao Zhu,
Hai-Hua Lu,
Wen-Xiu Xu
Department of Chemistry, Zhejiang University, 866 Yuhangtang Road, Hangzhou, Zhejiang, 310058 China
Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry and Research Center for Industries of the Future, Westlake University, 600 Dunyu Road, Hangzhou, Zhejiang, 310030 China
Search for more papers by this authorLi-Han Zhao
Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry and Research Center for Industries of the Future, Westlake University, 600 Dunyu Road, Hangzhou, Zhejiang, 310030 China
Search for more papers by this authorYao Zhu
Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry and Research Center for Industries of the Future, Westlake University, 600 Dunyu Road, Hangzhou, Zhejiang, 310030 China
Search for more papers by this authorCorresponding Author
Hai-Hua Lu
Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry and Research Center for Industries of the Future, Westlake University, 600 Dunyu Road, Hangzhou, Zhejiang, 310030 China
Institute of Natural Sciences, Westlake Institute for Advanced Study, 18 Shilongshan Road, Hangzhou, Zhejiang, 310024 China
E-mail: [email protected]Search for more papers by this authorWen-Xiu Xu,
Li-Han Zhao,
Yao Zhu,
Hai-Hua Lu,
Wen-Xiu Xu
Department of Chemistry, Zhejiang University, 866 Yuhangtang Road, Hangzhou, Zhejiang, 310058 China
Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry and Research Center for Industries of the Future, Westlake University, 600 Dunyu Road, Hangzhou, Zhejiang, 310030 China
Search for more papers by this authorLi-Han Zhao
Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry and Research Center for Industries of the Future, Westlake University, 600 Dunyu Road, Hangzhou, Zhejiang, 310030 China
Search for more papers by this authorYao Zhu
Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry and Research Center for Industries of the Future, Westlake University, 600 Dunyu Road, Hangzhou, Zhejiang, 310030 China
Search for more papers by this authorCorresponding Author
Hai-Hua Lu
Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry and Research Center for Industries of the Future, Westlake University, 600 Dunyu Road, Hangzhou, Zhejiang, 310030 China
Institute of Natural Sciences, Westlake Institute for Advanced Study, 18 Shilongshan Road, Hangzhou, Zhejiang, 310024 China
E-mail: [email protected]Search for more papers by this authorFirst published: 22 July 2024
†
† Dedicated to the Special Issue of Emerging Investigators in 2024.
Comprehensive Summary
The first catalytic asymmetric total synthesis of (+)-propolisbenzofuran B, enabled by a highly enantioselective rhodium-catalyzed hydrogenation of a tetrasubstituted olefin, was described. Other noteworthy aspects include the construction of the central hydrodibenzo[b,d]furan core through a sequence of Zn(II)-mediated regioselective benzofuran formation and Dieckmann condensation, as well as C-H oxidations, involving a visible light-induced Fe(III)-catalyzed benzylic C(sp3)-H oxidation. Additionally, the absolute configuration was confirmed by X-ray analysis of a carbonate intermediate.
Supporting Information
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Appendix S1: Supporting Information |
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