Synthetic studies towards ML-3000 - A concise synthesis of this non-steroidal anti-inflammatory drug

被引:11
作者
Cossy, J [1 ]
Belotti, D [1 ]
机构
[1] Ecole Super Phys & Chim Ind, CNRS, Chim Organ Lab, F-75231 Paris 05, France
关键词
D O I
10.1016/S0040-4020(99)00176-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
ML-3000 was obtained from 1-chloro-3-phenyl-2-propyne in 8 steps with an overall yield of 19%. The key steps are a thermal acid-promoted bicyclization of an omega-acetylenic amino ester and a Suzuki cross-coupling reaction between a heteroaryl triflate and (4-chlorophenyl)boronic acid. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5145 / 5156
页数:12
相关论文
共 28 条
  • [1] Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures
    AbdelMagid, AF
    Carson, KG
    Harris, BD
    Maryanoff, CA
    Shah, RD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) : 3849 - 3862
  • [2] AMADIO P, 1993, POSTGRAD MED, V93, P73
  • [3] ELECTROPHILIC CYCLIZATION OF POLYENE ALLYLSILANES - SYNTHESIS OF ALBICANYL ACETATE
    ARMSTRONG, RJ
    HARRIS, FL
    WEILER, L
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1982, 60 (05): : 673 - 675
  • [4] INDOMETHACIN-INDUCED LEUKOCYTE ADHESION IN MESENTERIC VENULES - ROLE OF LIPOXYGENASE PRODUCTS
    ASAKO, H
    KUBES, P
    WALLACE, J
    GAGINELLA, T
    WOLF, RE
    GRANGER, DN
    [J]. AMERICAN JOURNAL OF PHYSIOLOGY, 1992, 262 (05): : G903 - G908
  • [5] Belotti D, 1997, SYNLETT, P1249
  • [6] Cyclization of delta,epsilon-acetylenic amines and aminoacids into cyclic enamines. A very efficient and simple access to polysubstituted pyrrolidines.
    Cossy, J
    Belotti, D
    Bellosta, V
    Boggio, C
    [J]. TETRAHEDRON LETTERS, 1997, 38 (15) : 2677 - 2680
  • [7] Synthesis of ML-3000, an inhibitor of cyclooxygenase and 5-lipoxygenase
    Cossy, J
    Belotti, D
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (23) : 7900 - 7901
  • [8] COSSY J, 1996, Patent No. 9612760
  • [9] COSSY J, 1998, Patent No. 17666
  • [10] COSSY J, 1998, Patent No. 05812