A combinatorial synthesis of a macrosphelide library utilizing a palladium-catalyzed carbonylation on a polymer support

被引:85
作者
Takahashi, T
Kusaka, S
Doi, T
Sunazuka, T
Omura, S
机构
[1] Tokyo Inst Technol, Dept Appl Chem, Tokyo 1528552, Japan
[2] Kitasato Univ, Kitasato Inst Life Sci, Tokyo 1088641, Japan
[3] Kitasato Univ, Sch Pharmaceut Sci, Tokyo 1088641, Japan
[4] Kitasato Inst Shirokane, Tokyo 1088641, Japan
关键词
chemoselectivity combinatorial chemistry macrosphelides; palladium; solid-phase synthesis;
D O I
10.1002/anie.200352229
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Supported total synthesis: The combinatorial synthesis of a 122-membered macrosphelide library including macrosphelides A, C, E, and F (see picture) has been achieved based on a unique strategy for a three-component coupling utilizing a palladium-catalyzed chemoselective carbonylation and an unprecedented macrolactonization on a polymer support.
引用
收藏
页码:5230 / 5234
页数:5
相关论文
共 39 条
  • [1] ANACARDIO R, 1995, SYNTHESIS-STUTTGART, P831
  • [2] LEUKOCYTE-ENDOTHELIAL CELL RECOGNITION - 3 (OR MORE) STEPS TO SPECIFICITY AND DIVERSITY
    BUTCHER, EC
    [J]. CELL, 1991, 67 (06) : 1033 - 1036
  • [3] COWELL A, 1979, TETRAHEDRON LETT, P133
  • [4] The exceptional chelating ability of dimethylaluminum chloride and methylaluminum dichloride.: The merged stereochemical impact of α- and β-stereocenters in chelate-controlled carbonyl addition reactions with enolsilane and hydride nucleophiles
    Evans, DA
    Allison, BD
    Yang, MG
    Masse, CE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (44) : 10840 - 10852
  • [5] Chelation-controlled stannylacetylene additions to β-alkoxy aldehydes promoted by alkylaluminum halide Lewis acids
    Evans, DA
    Halstead, DP
    Allison, BD
    [J]. TETRAHEDRON LETTERS, 1999, 40 (24) : 4461 - 4462
  • [6] Chelate-controlled carbonyl addition reactions. The exceptional chelating ability of dimethylaluminum chloride and methylaluminum dichloride
    Evans, DA
    Allison, BD
    Yang, MG
    [J]. TETRAHEDRON LETTERS, 1999, 40 (24) : 4457 - 4460
  • [7] Macrosphelide B suppressed metastasis through inhibition of adhesion of sLex/E-selectin molecules
    Fukami, A
    Iijima, K
    Hayashi, M
    Komiyama, K
    Omura, S
    [J]. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2002, 291 (04) : 1065 - 1070
  • [8] GUANTI G, 1987, GAZZ CHIM ITAL, V117, P681
  • [9] Synthesis of a new troponoid liquid crystalline library on solid support
    Hashimoto, M
    Mori, A
    Inoue, H
    Nagamiya, H
    Doi, T
    Takahashi, T
    [J]. TETRAHEDRON LETTERS, 2003, 44 (06) : 1251 - 1254
  • [10] Macrosphelide, a novel inhibitor of cell-cell adhesion molecule .1. Taxonomy, fermentation, isolation and biological activities
    Hayashi, M
    Kim, YP
    Hiraoka, H
    Natori, M
    Takamatsu, S
    Kawakubo, T
    Masuma, R
    Komiyama, K
    Omura, S
    [J]. JOURNAL OF ANTIBIOTICS, 1995, 48 (12) : 1435 - 1439