An Approach to the Synthesis of Tetrahydroisoquinoline Alkaloids by Alkene Hydroamination: Synthesis of Coralydine

被引:11
|
作者
Pouilhes, Annie [1 ]
Baltaze, Jean-Pierre [1 ]
Kouklovsky, Cyrille [1 ]
机构
[1] Univ Paris Sud, Inst Chim Mol & Mat Orsay, CNRS, UMR 8182, F-91405 Orsay, France
关键词
alkaloids; total synthesis; nitrogen; heterocycles; ASYMMETRIC-SYNTHESIS; ISOQUINOLINE ALKALOIDS; STRATEGY;
D O I
10.1055/s-0033-1339375
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The protoberberine alkaloid coralydine was synthesized in a short sequence by a strategy including an intramolecular alkene hydroamination as the key step, followed by a Pictet-Spengler cyclization.
引用
收藏
页码:1805 / 1808
页数:4
相关论文
共 50 条
  • [1] A General Methodology for the Enantioselective Synthesis of 1-Substituted Tetrahydroisoquinoline Alkaloids
    Amat, Mercedes
    Elias, Viviane
    Llor, Nuria
    Subrizi, Fabiana
    Molins, Elies
    Bosch, Joan
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (21) : 4017 - 4026
  • [2] Phosphate mediated biomimetic synthesis of tetrahydroisoquinoline alkaloids
    Pesnot, Thomas
    Gershater, Markus C.
    Ward, John M.
    Hailes, Helen C.
    CHEMICAL COMMUNICATIONS, 2011, 47 (11) : 3242 - 3244
  • [3] Total synthesis of racemic 1-aryl-tetrahydroisoquinoline alkaloids
    Abranyi-Balogh, Peter
    Foeldesi, Tamas
    Milen, Matyas
    MONATSHEFTE FUR CHEMIE, 2015, 146 (11): : 1907 - 1912
  • [4] Progress in the Total Synthesis of Antitumor Tetrahydroisoquinoline Alkaloids
    Gao, Yi
    Tu, Ni
    Liu, Xiaoting
    Lu, Kangkang
    Chen, Siyu
    Guo, Ju
    CHEMISTRY & BIODIVERSITY, 2023, 20 (05)
  • [5] A simple approach for the synthesis of azocine alkaloids: The total synthesis of megallanesine
    Volvoikar, Prajesh S.
    Tilve, Santosh G.
    TETRAHEDRON LETTERS, 2018, 59 (26) : 2567 - 2569
  • [6] Stereoselective synthesis of tetrahydroisoquinoline alkaloids: (-)-trolline, (+)-crispin A, (+)-oleracein E
    Kawai, Nobuyuki
    Matsuda, Mika
    Uenishi, Jun'ichi
    TETRAHEDRON, 2011, 67 (45) : 8648 - 8653
  • [7] Total synthesis of racemic 1-aryl-tetrahydroisoquinoline alkaloids
    Péter Ábrányi-Balogh
    Tamás Földesi
    Mátyás Milen
    Monatshefte für Chemie - Chemical Monthly, 2015, 146 : 1907 - 1912
  • [8] Synthesis of Tetrahydroisoquinoline Alkaloids via Anodic Cyanation as the Key Step
    Louafi, Fadila
    Hurvois, Jean-Pierre
    Chibani, Aissa
    Roisnel, Thierry
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (16) : 5721 - 5724
  • [9] Recent Advances in Total Synthesis of Tetrahydroisoquinoline Alkaloids Quinocarcin and Lemonomycin
    Guo, Ju
    Yang, Yang
    Shen, Lanhua
    Li, Jingyi
    Li, Fuan
    Wang, Sifan
    MINI-REVIEWS IN ORGANIC CHEMISTRY, 2024, 21 (08) : 852 - 861
  • [10] Total synthesis of (-)-epimyrtine by a gold-catalyzed hydroamination approach
    Thi Thanh Huyen Trinh
    Nguyen, Khanh Hung
    Amaral, Patricia De Aguiar
    Gouault, Nicolas
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 2042 - 2047