Visible-Light-Induced Radical Cascade Cyclization: Synthesis of (20S)-Camptothecin, SN-38 and Irinotecan

被引:16
|
作者
Yuan, Yao [1 ]
Dong, Wuheng [1 ]
Gao, Xiaoshuang [1 ]
Xie, Xiaomin [1 ]
Curran, Dennis P. [2 ]
Zhang, Zhaoguo [1 ]
机构
[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China
[2] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
基金
中国国家自然科学基金;
关键词
photocatalysis; radicals; camptothecin; irinotecan; SN-38; ruthenium; ASYMMETRIC-SYNTHESIS; ANTITUMOR AGENTS; CAMPTOTHECIN; ISONITRILES; (S)-CAMPTOTHECIN; CANCER;
D O I
10.1002/cjoc.201800358
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(20S)-Camptothecin, irinotecan and SN-38 were successfully synthesized by a photocatalyzed radical cascade cyclization from an N-propargyl iodopyridinone and an arylisonitrile under visible light with a ruthenium catalyst. This synthetic method provided a useful entry into composing camptothecin family of antitumor agents in good yields under mild reaction conditions without the use of heavy metal reagents.
引用
收藏
页码:1035 / 1040
页数:6
相关论文
共 50 条
  • [21] Synthesis of Perfluorinated Isoquinolinediones through Visible-Light-Induced Cyclization of Alkenes
    Tang, Shi
    Deng, You-Lin
    Li, Jie
    Wang, Wen-Xin
    Ding, Guo-Liang
    Wang, Ming-Wei
    Xiao, Zhu-Ping
    Wang, Ying-Chun
    Sheng, Rui-Long
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (24): : 12599 - 12605
  • [22] Synthesis of functionalized pyrroloindolines via a visible-light-induced radical cascade reaction: rapid synthesis of (±)-flustraminol B
    Wu, Kui
    Du, Yuliu
    Wei, Zheng
    Wang, Ting
    CHEMICAL COMMUNICATIONS, 2018, 54 (54) : 7443 - 7446
  • [23] Chemoselective Synthesis of 3-Bromomethyloxindoles via Visible-Light-Induced Radical Cascade Bromocyclization of Alkenes
    Zhang, Ming-Zhong
    Yang, Xin
    Yin, Jin-Xing
    Deng, Ya
    Tan, Hong-Ying
    Bai, Yu-Heng
    Li, Ya-Lin
    Wen, Jiangwei
    Chen, Tieqiao
    ORGANIC LETTERS, 2024, 26 (18) : 3923 - 3928
  • [24] Diastereoselective visible-light-induced radical cascade trifluoromethylation/sulfuration/cyclization of 1,6-enynes with S-aryl trifluoromethanesulfonothioate (TTSA)
    Jiang, Yuhao
    Sun, Jiapeng
    Hu, Qi
    Huang, Jianmin
    Song, Yingming
    Cao, Hua
    Yu, Yue
    ORGANIC CHEMISTRY FRONTIERS, 2025,
  • [25] Visible-light-induced reusable decatungstate-photocatalyzed radical cascade alkylation/cyclization of isocyanides with simple alkanes, ethers and ketones
    Wang, Ke-Li
    Ji, Hong-Tao
    Peng, Qiong-Hui
    Jiang, Jun
    Ou, Li-Juan
    He, Wei-Min
    GREEN SYNTHESIS AND CATALYSIS, 2025, 6 (01): : 106 - 109
  • [26] Visible-Light-Induced Radical Cyclization of Trifluoroacetimidoyl Chlorides with Alkynes: Catalytic Synthesis of 2-Trifluoromethyl Quinolines
    Dong, Xichang
    Xu, Youwei
    Liu, Jing Jing
    Hu, Yumin
    Xiao, Tiebo
    Zhou, Lei
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (50) : 16928 - 16933
  • [27] Convenient synthesis of 2-chloro-3-substituted quinoxalines by visible-light-induced radical cascade cyclization of ortho-diisocyanoarenes with sulfinic acids
    Natarajan, Palani
    Partigya
    Meena
    NEW JOURNAL OF CHEMISTRY, 2024, 48 (10) : 4521 - 4528
  • [28] Visible-Light-Induced Cascade Phosphinoylation/Cyclization of Phenacylmalononitriles with Secondary H-phosphine Oxides
    Xiong, Biquan
    Shi, Chonghao
    Xu, Weifeng
    Liu, Yu
    Zhu, Longzhi
    Tang, Ke-Wen
    Yin, Shuang-Feng
    Wong, Wai-Yeung
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (24) : 4392 - 4401
  • [29] Synthesis of 1,4-Dicarbonyl Compounds via Visible-Light-Induced Decarboxylative Radical Cascade Reactions
    Su, Zhiyou
    Zhang, Jia
    Lin, Hou-Wen
    Liao, Hongze
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (20) : 3444 - 3449
  • [30] Visible-Light-Induced Radical Polynitration of Arylboronic Acids: Synthesis of Polynitrophenols
    Zhang, Qi
    Babu, Kaki Raveendra
    Huang, Zhouliang
    Song, Jinna
    Bi, Xihe
    SYNTHESIS-STUTTGART, 2018, 50 (15): : 2891 - 2896