Synthesis of furanophane derivatives through [8+2]-cycloaddition of dienylisobenzofurans and alkynes

被引:33
作者
Luo, YM
Herndon, JW
Cervantes-Lee, F
机构
[1] New Mexico State Univ, Dept Chem & Biochem, Las Cruces, NM 88003 USA
[2] Univ Texas, Dept Chem, El Paso, TX 79968 USA
关键词
D O I
10.1021/ja037500n
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The coupling of various dienylisobenzofurans with dimethyl acetylenedicarboxylate (DMAD) has been examined. In most cases, this reaction proceeds via [8+2]-cycloaddition to afford furan-bridged decatetraene ring systems. The major competing reaction pathway is [4+2]-cycloaddition between DMAD and the isobenzofuran nucleus. Isobenzofuran intermediates were generated using either a chromium carbene-based method or an acid-catalyzed method. Copyright © 2003 American Chemical Society.
引用
收藏
页码:12720 / 12721
页数:2
相关论文
共 23 条
  • [1] Steric and electronic limitations for the Dotz benzannulation of aromatic alkynes
    Anderson, JC
    Cran, JW
    King, NP
    [J]. TETRAHEDRON LETTERS, 2002, 43 (21) : 3849 - 3852
  • [2] Quantum chemical analysis and experimental study of the cycloaddition reaction between aminoacetylenes and 6-nitroindolizines. NMR and ab initio evidence for the [4+2] adduct formation
    Babaev, EV
    Simonyan, VV
    Pasichnichenko, KY
    Nosova, VM
    Kisin, AV
    Jug, K
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (25) : 9057 - 9062
  • [3] FULVENES WITH INVERSE RING POLARIZATION .16. REGIOCHEMISTRY OF THE INTERMOLECULAR [8+2] CYCLO-ADDITION OF ELECTRON-RICH HEPTAFULVENES - SYNTHESES OF 1,2,3-TRISUBSTITUTED HYDROAZULENES
    BAUMLER, A
    DAUB, J
    PICKL, W
    RIEGER, W
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (05): : 1857 - 1867
  • [4] Bernardelli P, 1998, HETEROCYCLES, V49, P531
  • [5] Cycloaldol approach to the isobenzofuran core of eunicellin diterpenes
    Chai, YH
    Vicic, DA
    McIntosh, MC
    [J]. ORGANIC LETTERS, 2003, 5 (07) : 1039 - 1042
  • [6] Chen XT, 1998, ANGEW CHEM INT EDIT, V37, P185, DOI 10.1002/(SICI)1521-3773(19980202)37:1/2<185::AID-ANIE185>3.0.CO
  • [7] 2-L
  • [8] Enantioselective total synthesis of briarellins E and F: The first total syntheses of briarellin diterpenes
    Corminboeuf, O
    Overman, LE
    Pennington, LD
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (22) : 6650 - 6652
  • [9] Total synthesis of the reputed structure of alcyonin and reassignment of its structure
    Corminboeuf, O
    Overman, LE
    Pennington, LD
    [J]. ORGANIC LETTERS, 2003, 5 (09) : 1543 - 1546
  • [10] FULVENES WITH INVERSE RING POLARIZATION .15. [8+2] CYCLO-ADDITIONS OF ELECTRON-RICH HEPTAFULVENES - SCOPE OF THE REACTION AND STEREOCHEMISTRY
    DAUB, J
    HIRMER, G
    JAKOB, L
    MAAS, G
    PICKL, W
    PIRZER, E
    RAPP, KM
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (05): : 1836 - 1856