Divergent Synthesis of Skeletally Distinct Arboridinine and Arborisidine
Cheng Wang
Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641 China
These authors contributed equally to this work.
Search for more papers by this authorYubing Pang
Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641 China
These authors contributed equally to this work.
Search for more papers by this authorYuecheng Wu
Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641 China
Search for more papers by this authorNanping Zhang
Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641 China
Search for more papers by this authorRui Yang
Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641 China
Search for more papers by this authorYing Li
School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, 529020 P. R. China
Search for more papers by this authorPengquan Chen
Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641 China
Search for more papers by this authorProf. Dr. Huanfeng Jiang
Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641 China
Search for more papers by this authorProf. Dr. Xue-Tao Xu
School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, 529020 P. R. China
Search for more papers by this authorProf. Dr. Toh-Seok Kam
Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia
Search for more papers by this authorProf. Dr. Ting Fan
Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Zhiqiang Ma
Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641 China
Search for more papers by this authorCheng Wang
Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641 China
These authors contributed equally to this work.
Search for more papers by this authorYubing Pang
Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641 China
These authors contributed equally to this work.
Search for more papers by this authorYuecheng Wu
Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641 China
Search for more papers by this authorNanping Zhang
Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641 China
Search for more papers by this authorRui Yang
Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641 China
Search for more papers by this authorYing Li
School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, 529020 P. R. China
Search for more papers by this authorPengquan Chen
Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641 China
Search for more papers by this authorProf. Dr. Huanfeng Jiang
Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641 China
Search for more papers by this authorProf. Dr. Xue-Tao Xu
School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, 529020 P. R. China
Search for more papers by this authorProf. Dr. Toh-Seok Kam
Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia
Search for more papers by this authorProf. Dr. Ting Fan
Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Zhiqiang Ma
Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641 China
Search for more papers by this authorGraphical Abstract
A divergent synthesis of skeletally distinct arboridinine (1) and arborisidine (2) was achieved. The central divergent strategy was inspired by the divergent biosynthetic cyclization mode of arboridinine (1) and arborisidine (2) and their hidden topological connection.
Abstract
A divergent synthesis of skeletally distinct arboridinine and arborisidine was achieved. The central divergent strategy was inspired by the divergent biosynthetic cyclization mode of arboridinine and arborisidine and their hidden topological connection. The branch point was reached through a Michael and Mannich cascade process. A site-selective intramolecular Mannich reaction was developed to construct the tetracyclic core of arboridinine, while a site-selective intramolecular α-amination of ketone was used to access the tetracyclic core of arborisidine. A strategic Peterson olefination through intramolecular nucleophile delivery was able to set up the exocyclic olefin of arboridinine.
Conflict of interest
The authors declare no conflict of interest.
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