Concise and practical synthesis of latrunculin A by ring-closing enyne-yne metathesis

被引:181
|
作者
Fürstner, A [1 ]
Turet, L [1 ]
机构
[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
关键词
alkynes; cross-coupling; macrocycles; metathesis; natural products;
D O I
10.1002/anie.200500390
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Selective actin-binding is the most prominent biochemical property of the scarce marine natural product latrunculin A (see formula). Modern metal-catalyzed C-C bond-formation reactions, including a ring-closing enyne-yne metathesis (shown in red), now open a convenient, flexible, and productive entry to this important probe molecule for chemical biology. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:3462 / 3466
页数:5
相关论文
共 50 条
  • [1] A concise enantioselective synthesis of the AB ring system of the manzamine alkaloids by ring-closing enyne metathesis
    Clark, JS
    Townsend, RJ
    Blake, AJ
    Teat, SJ
    Johns, A
    TETRAHEDRON LETTERS, 2001, 42 (18) : 3235 - 3238
  • [2] Group-selective ring-closing enyne metathesis
    Maifeld, SV
    Lee, D
    CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (21) : 6118 - 6126
  • [3] A Ring-Closing Enyne Metathesis Approach to Functionalized Semicyclic Dienes: The Total Synthesis of (-)-Tetrangomycin
    Moodie, Lindon W. K.
    Larsen, David S.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (08) : 1684 - 1694
  • [4] (E)-Cycloalkenes and (E,E)-cycloalkadienes by ring closing diyne- or enyne-yne metathesis/semi-reduction
    Lacombe, F
    Radkowski, K
    Seidel, G
    Fürstner, A
    TETRAHEDRON, 2004, 60 (34) : 7315 - 7324
  • [5] Concise Synthesis of Substituted Quinolizin-4-ones by Ring-Closing Metathesis
    Alanine, Thomas A.
    Galloway, Warren R. J. D.
    McGuire, Thomas M.
    Spring, David R.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (26) : 5767 - 5776
  • [6] Cyclic Poly(ε-caprolactone) Synthesized by Combination of Ring-Opening Polymerization with Ring-Closing Metathesis, Ring Closing Enyne Metathesis, or "Click" Reaction
    Xie, Meiran
    Shi, Jiaxin
    Ding, Liang
    Li, Jinxin
    Han, Huijing
    Zhang, Yiqun
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2009, 47 (12) : 3022 - 3033
  • [7] The Ruthenium-Catalyzed Domino Cross Enyne Metathesis/Ring-Closing Metathesis in the Synthesis of Enantioenriched Nitrogen-Containing Heterocycles
    Llobat, Alberto
    Escorihuela, Jorge
    Sedgwick, Daniel M.
    Rodenes, Miriam
    Roman, Raquel
    Soloshonok, Vadim A.
    Han, Jianlin
    Medio-Simon, Mercedes
    Fustero, Santos
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (27) : 4193 - 4207
  • [8] Exploration of Ring-Closing Enyne Metathesis for the Synthesis of Azonino[5,4-b]indoles
    Sole, Daniel
    Lluiesa Bennasar, M. -
    Roca, Tomas
    Valldosera, Magdalena
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (07) : 1355 - 1366
  • [9] Synthesis of Carbocyclic Aromatic Compounds Using Ruthenium-Catalyzed Ring-Closing Enyne Metathesis
    Takahashi, Hidetoshi
    Yoshida, Kazuhiro
    Yanagisawa, Akira
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10) : 3632 - 3640
  • [10] Preparation of cyclic ethers for polyether synthesis by catalytic ring-closing enyne metathesis of alkynyl ethers
    Clark, JS
    Elustondo, F
    Trevitt, GP
    Boyall, D
    Robertson, J
    Blake, AJ
    Wilson, C
    Stammen, B
    TETRAHEDRON, 2002, 58 (10) : 1973 - 1982