Synthesis of cycloisodityrosine revisited: A selective ring forming process

被引:14
作者
Bigot, A [1 ]
Zhu, JP [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
D O I
10.1016/S0040-4039(97)10664-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cycloetherification of dipeptide (L,L) N-Boc-(4-fluoro-3-nitro)Phe-Dopa methyl ester (11) gave exclusively the (m,p)-cyclophane (14) at the expense of the 15-membered (p,p)cyclophane (16). An efficient synthesis of cycloisodityrosine was consequently developed (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:551 / 554
页数:4
相关论文
共 26 条
  • [1] SNAR-BASED MACROCYCLIZATION - AN APPLICATION TO THE SYNTHESIS OF VANCOMYCIN FAMILY MODELS
    BEUGELMANS, R
    SINGH, GP
    BOISCHOUSSY, M
    CHASTANET, J
    ZHU, JP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) : 5535 - 5542
  • [2] A formal total synthesis of deoxybouvardin
    Bigot, A
    Beugelmans, R
    Zhu, JP
    [J]. TETRAHEDRON, 1997, 53 (31) : 10753 - 10764
  • [3] BIGOT A, UNPUB
  • [4] 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
  • [5] SELECTIVELY PROTECTED L-DOPA DERIVATIVES - APPLICATION OF THE BENZYLIC HYDROPEROXIDE REARRANGEMENT
    BOGER, DL
    YOHANNES, D
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (23) : 5283 - 5286
  • [6] INTRAMOLECULAR ULLMANN CONDENSATION REACTION - AN EFFECTIVE APPROACH TO MACROCYCLIC DIARYL ETHERS
    BOGER, DL
    YOHANNES, D
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) : 1763 - 1767
  • [7] Synthesis of the vancomycin CD and DE ring systems
    Boger, DL
    Borzilleri, RM
    Nukui, S
    Beresis, RT
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14) : 4721 - 4736
  • [8] Synthesis of model tricyclic C-O-D-O-E-F-O-G ring of teicoplanin
    BoisChoussy, M
    Vergne, C
    Neuville, L
    Beugelmans, R
    Zhu, JP
    [J]. TETRAHEDRON LETTERS, 1997, 38 (33) : 5795 - 5798
  • [9] Synthesis of modified carboxyl binding pockets of vancomycin and teicoplanin
    BoisChoussy, M
    Neuville, L
    Beugelmans, R
    Zhu, JP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) : 9309 - 9322
  • [10] BORCHARDT A, 1995, SYNLETT, P539