Studies toward the total synthesis of RP-66453

被引:18
作者
Boisnard, S [1 ]
Zhu, JP [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
neurotensine receptor antagonist; RP; 66453; macrocycle; biaryl; biaryl ether; intramolecular SNAr reaction;
D O I
10.1016/S0040-4039(02)00307-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of a bicyclic A-B-O-C ring system of RP-66453, an neurotensine receptor antagonist, with an endo aryl-aryl and an endo aryl-aryl ether bond is described. An alternative synthetic strategy starting from the construction of functionalized B-O-C cycloisodityrosine unit is also detailed. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2577 / 2580
页数:4
相关论文
共 33 条
  • [1] Synthesis of cycloisodityrosine revisited: A selective ring forming process
    Bigot, A
    Zhu, JP
    [J]. TETRAHEDRON LETTERS, 1998, 39 (07) : 551 - 554
  • [2] Total synthesis of an antitumor agent RA-VII via an efficient preparation of cycloisodityrosine
    Bigot, A
    Elise, M
    Dau, TH
    Zhu, JP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (17) : 6283 - 6296
  • [3] Synthesis of (9R,12S)- and (9S,12S)-cycloisodityrosine and their N-methyl derivatives
    Boger, DL
    Zhou, JC
    Borzilleri, RM
    Nukui, S
    Castle, SL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07) : 2054 - 2069
  • [4] TOTAL SYNTHESIS OF BOUVARDIN, O-METHYLBOUVARDIN, AND O-METHYL-N-9-DESMETHYLBOUVARDIN
    BOGER, DL
    PATANE, MA
    ZHOU, JC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (19) : 8544 - 8556
  • [5] Studies on the total synthesis of RP 66453: Synthesis of fully functionalized 15-membered biaryl-containing macrocycle
    Boisnard, S
    Carbonnelle, AC
    Zhu, JP
    [J]. ORGANIC LETTERS, 2001, 3 (13) : 2061 - 2064
  • [6] SYNTHESIS OF ANALOGS OF THE BIPHENOMYCIN ANTIBIOTICS
    BROWN, AG
    EDWARDS, PD
    [J]. TETRAHEDRON LETTERS, 1990, 31 (45) : 6581 - 6584
  • [7] BROWN AG, 1992, J CHEM SOC P1, V1, P123
  • [8] STRUCTURE OF BIPHENOMYCIN-A DERIVED FROM TWO-DIMENSIONAL NMR-SPECTROSCOPY AND MOLECULAR MODELING
    BROWN, FK
    HEMPEL, JC
    DIXON, JS
    AMATO, S
    MUELLER, L
    JEFFS, PW
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (19) : 7328 - 7333
  • [9] Nucleophilic aromatic substitution - A possible key step in total syntheses of vancomycin
    Burgess, K
    Lim, D
    Martinez, CI
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (10): : 1077 - 1078
  • [10] A novel synthesis of biaryl-containing macrocycles by a domino miyaura arylboronate formation: Intramolecular Suzuki reaction
    Carbonnelle, AC
    Zhu, JP
    [J]. ORGANIC LETTERS, 2000, 2 (22) : 3477 - 3480