Palladium-catalyzed sequential reaction via Sonogashira coupling, isomerization, Claisen rearrangement and [4+2] cycloaddition sequence for the rapid synthesis of tricyclo[3.2.1.02,7]oct-3-ene derivatives

被引:17
作者
Zhu, Shugao [1 ]
Wu, Luling [1 ]
Huang, Xian [1 ,2 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Zhejiang, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
来源
RSC ADVANCES | 2012年 / 2卷 / 01期
基金
中国国家自然科学基金;
关键词
ORGANIC-SYNTHESIS; DOMINO REACTIONS; HIGHLY FLUORESCENT; CASCADE REACTIONS; TANDEM REACTIONS; TRANSFORMATIONS; STEREOCHEMISTRY; DICHOTOMIES; METHODOLOGY; STRATEGIES;
D O I
10.1039/c1ra00452b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An interesting sequential reaction consisting of Sonogashira coupling, propargyl-allenyl isomerization, allenyl-benzyl Claisen rearrangement and [4 + 2] cycloaddition was developed. This reaction provides an efficient synthesis of fused tricyclo [3.2.1.0(2,7)]oct-3-enes.
引用
收藏
页码:132 / 134
页数:3
相关论文
共 40 条
  • [1] Synthesis of highly functionalised enantiopure bicyclo[3.2.1]-octane systems from carvone
    Abad, A
    Agulló, C
    Cuñat, AC
    de Alfonso, I
    Navarro, I
    Vera, N
    [J]. MOLECULES, 2004, 9 (05): : 287 - 299
  • [2] Two birds with one metallic stone: Single-pot catalysis of fundamentally different transformations
    Ajamian, A
    Gleason, JL
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (29) : 3754 - 3760
  • [3] NATURALLY-OCCURRING TERPENE DERIVATIVES .293. GERMACRANOLIDES AND DITERPENES FROM VIGUIERA SPECIES
    BOHLMANN, F
    JAKUPOVIC, J
    AHMED, M
    GRENZ, M
    SUDING, H
    ROBINSON, H
    KING, RM
    [J]. PHYTOCHEMISTRY, 1981, 20 (01) : 113 - 116
  • [4] Braun PU, 2000, ORG LETT, V2, P4181
  • [5] Coupling-isomerization synthesis of chalcones
    Braun, Roland U.
    Ansorge, Markus
    Mueller, Thomas J. J.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (35) : 9081 - 9094
  • [6] A novel one-pot pyrrole synthesis via a coupling-isomerization-Stetter-Paal-knorr sequence
    Braun, RU
    Zeitler, K
    Muller, TJJ
    [J]. ORGANIC LETTERS, 2001, 3 (21) : 3297 - 3300
  • [7] Benzofurans as Efficient Dienophiles in Normal Electron Demand [4+2] Cycloadditions
    Chopin, Nathalie
    Gerard, Helene
    Chataigner, Isabelle
    Piettre, Serge R.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (03) : 1237 - 1246
  • [8] STEREOSPECIFIC TOTAL SYNTHESIS OF (+/-)-CAFESTOL
    COREY, EJ
    WESS, G
    XIANG, YB
    SINGH, AK
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (15) : 4717 - 4718
  • [9] Tandem cross-metathesis/hydrogenation/cyclization reactions by using compatible catalysts
    Cossy, J
    Bargiggia, F
    BouzBouz, S
    [J]. ORGANIC LETTERS, 2003, 5 (04) : 459 - 462
  • [10] Dichotomies in microwave-assisted propargyl-isomerization-Claisen domino sequences dependent on base strengths
    D'Souza, Daniel M.
    Liao, Wei-Wei
    Rominger, Frank
    Mueller, Thomas J. J.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (03) : 532 - 539