Synthesis of the C1′-C11′ oxazole-containing side chain of leucascandrolide A.: Application of a sonogashira cross-coupling

被引：53
|
作者：
Dakin, LA
Langille, NF
Panek, JS
机构：
[1] Boston Univ, Metcalf Ctr Sci & Engn, Dept Chem, Boston, MA 02215 USA
[2] Boston Univ, Metcalf Ctr Sci & Engn, Ctr Streamlined Synth, Boston, MA 02215 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 19期
关键词：
D O I：
10.1021/jo0204000
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient, convergent synthesis of the C1'-C11' side chain (3) of leucascandrolide A (1) has been achieved. The key bond connection is made through the use of a palladium(0)-catalyzed Sonogashira cross-coupling between trifloyl oxazole (4) and alkynylmetal species (5).
引用
收藏
页码：6812 / 6815
页数：4
相关论文
共 50 条
  • [31] Palladium-mediated 11C-carbonylative cross-coupling of alkyl/aryl iodides with organostannanes:: An efficient synthesis of unsymmetrical alkyl/aryl [11C-carbonyl]ketones
    Karimi, F
    Barletta, J
    Långström, B
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (11) : 2374 - 2378
  • [32] Synthesis, crystal structures, and application of two new pincer type palladium(II)-Schiff base complexes in C-C cross-coupling reactions
    Agrahari, Bhumika
    Layek, Samaresh
    Anuradha
    Ganguly, Rakesh
    Pathak, Devendra D.
    INORGANICA CHIMICA ACTA, 2018, 471 : 345 - 354
  • [33] Synthesis of 1,3-disubstituted bicyclo[1.1.1]pentanes by cross-coupling induced by transition metals - formation of C-C bonds
    Yasukawa, Tomohiro
    Haheim, Katja S.
    Cossy, Janine
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (38) : 7666 - 7680
  • [34] Synthesis and characterization of Ni(II) complex functionalized silica-based magnetic nanocatalyst and its application in C-N and C-C cross-coupling reactions
    Nejad, Mohaddeseh Shahabi
    Seyedi, Neda
    Sheibani, Hassan
    Behzadi, Soheila
    MOLECULAR DIVERSITY, 2019, 23 (03) : 527 - 539
  • [35] Pd0-Mediated Cross-Coupling of [11C]Methyl Iodide with Carboxysilane for Synthesis of [11C]Acetic Acid and its Active Esters: 11C-Acetylation of Small, Medium, and Large Molecules
    Doi, Hisashi
    Goto, Miki
    Sato, Yuzuru
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (29) : 3970 - 3979
  • [36] Synthesis of 15-(4-[11C]methylphenyl)pentadecanoic acid (MePPA) via Stille cross-coupling reaction
    Al-Momani, E.
    Zlatopolskiy, B. D.
    Solbach, C.
    Reske, S. N.
    Machulla, H. -J.
    JOURNAL OF RADIOANALYTICAL AND NUCLEAR CHEMISTRY, 2011, 288 (03) : 881 - 886
  • [37] Synthesis of 15-(4-[11C]methylphenyl)pentadecanoic acid (MePPA) via Stille cross-coupling reaction
    E. Al-Momani
    B. D. Zlatopolskiy
    C. Solbach
    S. N. Reske
    H.-J. Machulla
    Journal of Radioanalytical and Nuclear Chemistry, 2011, 288 : 881 - 886
  • [38] Synthesis of 1,3-benzothiazines by intramolecular dehydrogenative C-S cross-coupling in a flow electrolysis cell
    Huang, Chong
    Xu, Hai-Chao
    SCIENCE CHINA-CHEMISTRY, 2019, 62 (11) : 1501 - 1503
  • [39] Synthesis of all carbon linked glycoside clusters round benzene scaffold via Sonogashira-Heck-Cassar cross-coupling of iodobenzenes with ethynyl C-glycosides
    Dondoni, A
    Marra, A
    Zampolli, MG
    SYNLETT, 2002, (11) : 1850 - 1854
  • [40] Alkyl Iodides and [11C]CO in Nickel-Mediated Cross-Coupling Reactions: Successful Use of Alkyl Electrophiles containing a β Hydrogen Atom in Metal-Mediated [11C]Carbonylation
    Rahman, Obaidur
    Langstrom, Bengt
    Halldin, Christer
    CHEMISTRYSELECT, 2016, 1 (10): : 2498 - 2501
12345