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研究论文

基于联苯硼酸的Cochlearol F和Didehydroconicol全合成研究

王凯a, 隋佳俊a, 龙纯洪a, 罗松娟a, 钏永明a, 秦红波a,*   

  1. 云南民族大学化学与环境学院 云南昆明 650000
  • 收稿日期:2024-04-30 修回日期:2024-06-20

Total syntheses of Cochlearol F and Didehydroconicol by biphenyl boronic acid.

Wang, Kaia, Sui, Jiajuna, Long, Chunhonga, Luo, Sunjuana, Chuan, Yongminga, Qin, Hongboa,*   

  1. Yunnan Minzu University of Chemistry and Environment College, Yunnan,Kunming 650000
  • Received:2024-04-30 Revised:2024-06-20
  • Contact: *E-mail:qinhb@ymu.edu.cn

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通过Suzuki偶联反应完成了Cochlearol F和Didehydroconicol的全合成。该合成的创新点为使用了联苯硼酸。Cochlearol F的全合成中,关键反应为联苯硼酸与烯醇三氟甲磺酸酯的偶联构建新的碳碳键,共需4步,总收率为25%;在后者的全合成中,关键反应为联苯硼酸的一氧化碳插入形成联苯内酯,共需7步,总收率为23%;本合成策略将为含联苯结构的天然产物的合成提供参考.

关键词: 全合成, Suzuki交叉偶联, Cochlearol F, Didehydroconicol

Total syntheses of Cochlearol F and Didehydroconicol were accomplished through the Suzuki coupling reaction, with the innovative use of biphenylboronic acid. In the total synthesis of Cochlearol F, the key reaction involved the coupling of biphenylboronic acid with enol trifluoromethanesulfonate to construct a new carbon-carbon bond, requiring four steps in total, with an overall yield of 25%. In the total synthesis of Didehydroconicol, the key reaction was the insertion of carbon monoxide into biphenylboronic acid to form a biphenyl lactone, requiring seven steps in total, with an overall yield of 23%. This synthetic strategy will provide a reference for the synthesis of natural products containing biphenyl unit.

Key words: Total synthesis, Suzuki cross-coupling, Cochlearol F, Didehydroconicolord