Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (1): 171-177.DOI: 10.6023/cjoc202208014 Previous Articles     Next Articles


Daphnezomines A和B的四环核心骨架合成

胡晶平a,b, 陈文清b, 蒋宇旸b, 徐晶b,c,*()   

  1. a 哈尔滨工业大学化工与化学学院 哈尔滨 150001
    b 南方科技大学化学系与格拉布斯研究院 广东省催化化学重点实验室深圳市小分子药物发现与合成重点实验室 广东深圳 518055
    c 深圳湾实验室 广东深圳 518132
  • 收稿日期:2022-08-13 修回日期:2022-09-02 发布日期:2022-10-10
  • 通讯作者: 徐晶
  • 基金资助:
    国家自然科学基金(21971104); 广东省教育厅高校重点科研项目(2021ZDZX2035); 深圳湾实验室(SZBL2019062801006); 深圳市诺贝尔奖科学家实验室(C17783101); 广东省本土创新团队项目(2019BT02Y335); 广东省高校创新团队(2020KCXTD016); 广东省催化化学重点实验室(2020B121201002); 深圳市科技创新委员会(ZDSYS20190902093215877)

Synthesis of Tetracyclic Core Structure of Daphnezomines A and B

Jingping Hua,b, Wenqing Chenb, Yuyang Jiangb, Jing Xub,c()   

  1. a School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001
    b Department of Chemistry and Shenzhen Grubbs Institute Guangdong Provincial Key Laboratory of Catalysis Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Southern University of Science and Technology, Shenzhen, Guangdong 518055
    c Shenzhen Bay Laboratory, Shenzhen, Guangdong 518132
  • Received:2022-08-13 Revised:2022-09-02 Published:2022-10-10
  • Contact: Jing Xu
  • Supported by:
    National Natural Science Foundation of China(21971104); Key Research Projects in Colleges and Universities of Education Department of Guangdong Province(2021ZDZX2035); Shenzhen Bay Laboratory(SZBL2019062801006); Shenzhen Nobel Prize Scientists Laboratory Project(C17783101); Guangdong Innovative Program(2019BT02Y335); Innovative Team of Universities in Guangdong Province(2020KCXTD016); Guangdong Provincial Key Laboratory of Catalysis(2020B121201002); Shenzhen Science and Technology Innovation Committee(ZDSYS20190902093215877)

Among the tiniest Daphniphyllum alkaloid subfamilies, daphnezomine A-type alkaloids consist of only three known members, namely daphnezomine A (1), daphnezomine B (2) and dapholdhamine B. These alkaloids contain a unique aza-adamantane core along with nine contiguous stereogenic centers, thus presenting remarkable synthetic challenges. The synthesis of tetracyclic core structure of 1 and 2 was reported. The key steps in our approach include a Huang’s amide-activa tion-annulation and a Hutchins-Kabalka reductive rearrangement.

Key words: total synthesis, Daphniphyllum alkaloids, daphnezomine A, daphnezomine B, aza-adamantane, Huang' s amide-activation-annulation, Hutchins-Kabalka reductive rearrangement