Facile synthesis of caerulomycin E by the formation of 2,2′-bipyridine core via a 2-pyridyl substituted 4H-pyran-4-one. Formal synthesis of caerulomycin A

被引：15
作者：
Bobrov, Denis N. [1 ]
Tyvorskii, Vladimir I. [2 ]
机构：
[1] Oasmia Pharmaceut AB, SE-75228 Uppsala, Sweden
[2] Belarusian State Univ, Dept Organ Chem, Minsk 220030, BELARUS
来源：
TETRAHEDRON | 2010年 / 66卷 / 29期
关键词：
Caerulomycins; 4H-Pyran-4-ones; 2,2 '-Bipyridines; Claisen condensation; STREPTOMYCES-CAERULEUS; INHIBITORS; DERIVATIVES;
D O I：
10.1016/j.tet.2010.05.024
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new approach to caerulomycins A and E via a 6-methyl-2-(2-pyridyl)-4H-pyran-4-one is described. The pyranone precursor is prepared by Claisen condensation of acetylacetone enol ether with ethyl picolinate. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5432 / 5434
页数：3
相关论文
共 21 条
  • [1] ALREJA BD, 1986, HETEROCYCLES, V24, P1637
  • [2] CAERULOMYCIN, AN ANTIFUNGAL ANTIBIOTIC WITH MARKED INVITRO AND INVIVO ACTIVITY AGAINST ENTAMOEBA-HISTOLYTICA
    CHATTERJEE, DK
    RAETHER, W
    IYER, N
    GANGULI, BN
    [J]. ZEITSCHRIFT FUR PARASITENKUNDE-PARASITOLOGY RESEARCH, 1984, 70 (05): : 569 - 573
  • [3] Ytterbium triflate catalyzed synthesis of β-keto enol ethers
    Curini, Massimo
    Epifano, Francesco
    Genovese, Salvatore
    [J]. TETRAHEDRON LETTERS, 2006, 47 (27) : 4697 - 4700
  • [4] A New and Flexible Synthesis of 4-Hydroxypyridines: Rapid Access to Caerulomycins A, E and Functionalized Terpyridines
    Dash, Jyotirmayee
    Reissig, Hans-Ulrich
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (28) : 6811 - 6814
  • [5] Magnesiation of Pyridine N-Oxides via Iodine or Bromine-Magnesium Exchange: A Useful Tool for Functionalizing Pyridine N-Oxides
    Duan, Xin-Fang
    Ma, Zi-Qian
    Zhang, Fang
    Zhang, Zhan-Bin
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (02) : 939 - 942
  • [6] CAERULOMYCIN, A NEW ANTIBIOTIC FROM STREPTOMYCES-CAERULEUS BALDACCI .1. PRODUCTION, ISOLATION, ASSAY, AND BIOLOGICAL PROPERTIES
    FUNK, A
    DIVEKAR, PV
    [J]. CANADIAN JOURNAL OF MICROBIOLOGY, 1959, 5 (04) : 317 - 321
  • [7] GELIN S, 1971, B SOC CHIM FR, P2179
  • [8] Versatile tools in the construction of substituted 2,2′-bipyridines-cross-coupling reactions with tin, zinc and boron compounds
    Hapke, Marko
    Brandt, Lars
    Luetzen, Arne
    [J]. CHEMICAL SOCIETY REVIEWS, 2008, 37 (12) : 2782 - 2797
  • [9] Discovery of pyrrolopyridine-pyridone based inhibitors of Met kinase: Synthesis, X-ray crystallographic analysis, and biological activities
    Kim, Kyoung Soon
    Zhang, Liping
    Schmidt, Robert
    Cai, Zhen-Wei
    Wei, Donna
    Williams, David K.
    Lombardo, Louis J.
    Trainor, George L.
    Xie, Dianlin
    Zhang, Yaquan
    An, Yongmi
    Sack, John S.
    Tokarski, John S.
    Darienzo, Celia
    Kamath, Amrita
    Marathe, Punit
    Zhang, Yueping
    Lippy, Jonathan
    Jeyaseelan, Robert, Sr.
    Wautlet, Barri
    Henley, Benjamin
    Gullo-Brown, Johnni
    Manne, Veeraswamy
    Hunt, John T.
    Fargnoli, Joseph
    Borzilleri, Robert M.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (17) : 5330 - 5341
  • [10] 4-Pyridone derivatives as new inhibitors of bacterial enoyl-ACP reductase FabI
    Kitagawa, Hideo
    Kumura, Ko
    Takahata, Sho
    Iida, Maiko
    Atsumi, Kunio
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (02) : 1106 - 1116
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