Facile access to versatile aza-macrolides through iridium-catalysed cascade allyl-amination/macrolactonization

被引:19
作者
Fu, Wei [1 ]
Wang, Lianhui [1 ]
Yang, Zi [1 ]
Shen, Jiang-Shan [2 ]
Tang, Fei [1 ]
Zhang, Jiayi [1 ]
Cui, Xiuling [1 ]
机构
[1] Huaqiao Univ, Sch Biomed Sci, Minist Educ,Engn Res Ctr Mol Med, Key Lab Fujian Mol Med,Key Lab Xiamen Marine & Ge, Xiamen 361021, Peoples R China
[2] Huaqiao Univ, Coll Mat Sci & Engn, Xiamen 361021, Peoples R China
关键词
VINYLETHYLENE CARBONATES; DECARBOXYLATIVE CYCLOADDITION; ENANTIOSELECTIVE SYNTHESIS; CONSTRUCTION; HETEROCYCLES; BOND; MACROLACTONIZATION; MACROCYCLIZATION; REARRANGEMENT; METATHESIS;
D O I
10.1039/c9cc07372h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Direct access to benzo-fused aza-macrolides was successfully achieved through iridium-catalysed intermolecular decarboxylative coupling of vinylethylene carbonates with isatoic anhydrides under relatively mild reaction conditions. Notably, this reaction proceeded through sequential allyl-amination/macrolactonization upon extrusion of CO2. Moreover, favourable fluorescence properties could be observed in the title macrocyclic products.
引用
收藏
页码:960 / 963
页数:4
相关论文
共 75 条
  • [1] Macrocyclic Compounds for Drug and Gene Delivery in Immune-Modulating Therapy
    Bai, Hongzhen
    Wang, Jianwei
    Li, Zhongbao
    Tang, Guping
    [J]. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2019, 20 (09)
  • [2] Total Synthesis of (-)-Spinosyn A via Carbonylative Macrolactonization
    Bai, Yu
    Shen, Xingyu
    Li, Yong
    Dai, Mingji
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (34) : 10838 - 10841
  • [3] Synthesis of Tetrahydropyran/Tetrahydrofuran-Containing Macrolides by Palladium-Catalyzed Alkoxycarbonylative Macrolactonizations
    Bai, Yu
    Davis, Dexter C.
    Dai, Mingji
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (25) : 6519 - 6522
  • [4] Palladium-Catalyzed Regio- and Enantioselective Synthesis of Allylic Amines Featuring Tetrasubstituted Tertiary Carbons
    Cai, Aijie
    Guo, Wusheng
    Martinez-Rodriguez, Luis
    Kleij, Arjan W.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (43) : 14194 - 14197
  • [5] Supramolecular Coordination: Self-Assembly of Finite Two- and Three-Dimensional Ensembles
    Chakrabarty, Rajesh
    Mukherjee, Partha Sarathi
    Stang, Peter J.
    [J]. CHEMICAL REVIEWS, 2011, 111 (11) : 6810 - 6918
  • [6] Iridium-Catalyzed Asymmetric Allylic Substitution Reactions
    Cheng, Qiang
    Tu, Hang-Fei
    Zheng, Chao
    Qu, Jian-Ping
    Helmchen, Guenter
    You, Shu-Li
    [J]. CHEMICAL REVIEWS, 2019, 119 (03) : 1855 - 1969
  • [7] Access to benzo-fused nine-membered heterocyclic alkenes with a trifluoromethyl carbinol moiety via a double decarboxylative formal ring-expansion process under palladium catalysis
    Das, Pulakesh
    Gondo, Satoshi
    Nagender, Punna
    Uno, Hiroto
    Tokunaga, Etsuko
    Shibata, Norio
    [J]. CHEMICAL SCIENCE, 2018, 9 (13) : 3276 - 3281
  • [8] Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis
    Deiters, A
    Martin, SF
    [J]. CHEMICAL REVIEWS, 2004, 104 (05) : 2199 - 2238
  • [9] From Oxiranes to Oligomers: Architectures of US FDA Approved Pharmaceuticals Containing Oxygen Heterocycles
    Delost, Michael D.
    Smith, David T.
    Anderson, Benton J.
    Njardarson, Jon T.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2018, 61 (24) : 10996 - 11020
  • [10] Development of a General, Sequential, Ring-Closing Metathesis/Intramolecular Cross-Coupling Reaction for the Synthesis of Polyunsaturated Macrolactones
    Denmark, Scott E.
    Muhuhi, Joseck M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (33) : 11768 - 11778