Isolation and Asymmetric Total Synthesis of Perforanoid A |
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| Authors: | Chao Lv Dr Xiaohui Yan Qian Tu Dr Yingtong Di Dr Chunmao Yuan Dr Xin Fang Prof?Dr Yaacove Ben‐David Lei Xia Prof?Dr Jianxian Gong Prof?Dr Yuemao Shen Prof?Dr Zhen Yang Prof?Dr Xiaojiang Hao |
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| Institution: | 1. School of Pharmaceutical Sciences, Shandong University, Shandong, PR China;2. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, PR China;3. Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen, China;4. The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, China |
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| Abstract: | A novel limonoid, perforanoid A, was isolated, and an asymmetric total synthesis was achieved in 10 steps. The key steps are chiral tertiary aminonaphthol mediated enantioselective alkenylation of an aldehyde to an allylic alcohol, Pd‐catalyzed coupling of the allylic alcohol with vinyl ether to form the γ‐lactone ring, and cyclopentenone ring formation through a Rh‐catalyzed Pauson–Khand reaction. Preliminary studies show that perforanoid A is cytotoxic towards HEL, K562, and CB3 tumor cell lines. |
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| Keywords: | asymmetric synthesis cytotoxicity limonoids Pauson– Khand reaction total synthesis |
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