Intramolecular Larock Indole Synthesis: Preparation of 3,4-Fused Tricyclic Indoles and Total Synthesis of Fargesine

被引:127
作者
Shan, Dong [1 ]
Gao, Yan [1 ]
Jia, Yanxing [1 ,2 ]
机构
[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
基金
中国国家自然科学基金;
关键词
natural products; nitrogen heterocycles; palladium; synthetic methods; total synthesis; EFFICIENT TOTAL-SYNTHESIS; FORMAL TOTAL-SYNTHESIS; ACID METHYL-ESTER; NATURAL-PRODUCTS; (+)-LYSERGIC ACID; INTERNAL ALKYNES; FUSED INDOLES; CYCLIZATION; HETEROANNULATION; DIAZONAMIDE;
D O I
10.1002/anie.201300571
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Core strength: A new and general strategy for the construction of 3,4-fused tricyclic indoles, which are the core structure of numerous natural products and bioactive molecules, has been developed. The method involves a one-step intramolecular Larock indolization and was successfully applied to the first total synthesis of fargesine. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:4902 / 4905
页数:4
相关论文
共 92 条
  • [1] [Anonymous], 2010, ANGEW CHEM INT EDIT, V49, P2000
  • [2] [Anonymous], 2010, ANGEW CHEM
  • [3] [Anonymous], 2012, ANGEW CHEM, DOI [DOI 10.1002/ANGE.201108970, 10.1002/anie.201108970]
  • [4] Total synthesis of marine natural products without using protecting groups
    Baran, Phil S.
    Maimone, Thomas J.
    Richter, Jeremy M.
    [J]. NATURE, 2007, 446 (7134) : 404 - 408
  • [5] Total Synthesis of (±)-Communesin F via a Cycloaddition with Indol-2-one
    Belmar, Johannes
    Funk, Raymond L.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (41) : 16941 - 16943
  • [6] Total Synthesis of N-Methylwelwitindolinone D Isonitrile
    Bhat, Vikram
    Allan, Kevin M.
    Rawal, Viresh H.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (15) : 5798 - 5801
  • [7] A Pd(0)-Mediated Indole (Macro)cyclization Reaction
    Breazzano, Steven P.
    Poudel, Yam B.
    Boger, Dale L.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (04) : 1600 - 1606
  • [8] Understanding and Modulating Indolyne Regioselectivities
    Bronner, Sarah M.
    Goetz, Adam E.
    Garg, Neil K.
    [J]. SYNLETT, 2011, (18) : 2599 - 2604
  • [9] Overturning Indolyne Regioselectivities and Synthesis of Indolactam V
    Bronner, Sarah M.
    Goetz, Adam E.
    Garg, Neil K.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (11) : 3832 - 3835
  • [10] A novel sequential aminodiene Diels-Alder strategy for the rapid construction of substituted analogues of Kornfeld's ketone
    Bur, SK
    Padwa, A
    [J]. ORGANIC LETTERS, 2002, 4 (23) : 4135 - 4137