Synthesis of the first fluorinated cantharidin analogues

被引：45
|
作者：
Essers, M [1 ]
Wibbeling, B [1 ]
Haufe, G [1 ]
机构：
[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 32期
关键词：
Diels-Alder reaction; fluorinated cantharidin analogues; fluorinated maleic anhydrides; furan; O-17; NMR;
D O I：
10.1016/S0040-4039(01)01056-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Fluorinated cantharidin analogues (4-7) have been synthesized for the first time. The key step in each synthesis is an exo-selective Diels-Alder reaction of furan with the appropriate fluorinated maleic anhydride. O-17 NMR measurements of 5-7 and the corresponding non-fluorinated parent compounds were undertaken to show the influence of the fluorine substituent(s) on the electronic properties of the oxygen atoms. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：5429 / 5433
页数：5
相关论文
共 50 条
  • [1] Synthesis of glycerophospholipid conjugates of cantharidin and its analogues
    Zhou, ZH
    Chen, RY
    SYNTHETIC COMMUNICATIONS, 2000, 30 (19) : 3527 - 3533
  • [2] Synthesis of Fluorinated Thiophenes and Their Analogues
    Serdyuk, Olag V.
    Abaev, Vladimir T.
    Butin, Alexander V.
    Nenajdenko, Valentine G.
    SYNTHESIS-STUTTGART, 2011, (16): : 2505 - 2529
  • [3] Synthesis of fluorinated thiodigalactoside analogues
    St-Gelais, Jacob
    Leclerc, Christina
    Giguere, Denis
    CARBOHYDRATE RESEARCH, 2022, 511
  • [4] Synthesis of fluorinated indoles as RNA analogues
    Bozilovic, Jelena
    Engels, Joachim W.
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2007, 26 (8-9): : 869 - 871
  • [5] Synthesis and applications of fluorinated nucleoside analogues
    Wojtowicz-Rajchel, Hanna
    JOURNAL OF FLUORINE CHEMISTRY, 2012, 143 : 11 - 48
  • [6] The first two cantharidin analogues displaying PP1 selectivity
    McCluskey, A
    Keane, MA
    Walkom, CC
    Bowyer, MC
    Sim, ATR
    Young, DJ
    Sakoff, JA
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (03) : 391 - 393
  • [7] Synthesis of fluorinated sphinganine and dihydroceramide analogues
    De Jonghe, S
    Van Overmeire, I
    Van Calenbergh, S
    Hendrix, C
    Busson, R
    De Keukeleire, D
    Herdewijn, P
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2000, 2000 (18) : 3177 - 3183
  • [8] Overview of Cantharidin and its Analogues
    Wang, Guofang
    Dong, Jian
    Deng, Liping
    CURRENT MEDICINAL CHEMISTRY, 2018, 25 (17) : 2034 - 2044
  • [9] Efficient synthesis of dipeptide analogues of α-fluorinated β-aminophosphonates
    Kazmierczak, Marcin
    Koroniak, Henryk
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2020, 16 : 756 - 762
  • [10] Synthesis and biological activity of fluorinated combretastatin analogues
    Alloatti, Domenico
    Giannini, Giuseppe
    Cabri, Walter
    Lustrati, Isabella
    Marzi, Mauro
    Ciacci, Andrea
    Gallo, Grazia
    Tinti, M. Ornella
    Marcellini, Marcella
    Riccioni, Teresa
    Guglielmi, Mario B.
    Carminati, Paolo
    Pisano, Claudio
    JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (09) : 2708 - 2721
12345