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
  • [11] 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
  • [12] Approaches to the synthesis of the vancomycin antibiotics. Synthesis of orienticin C (bis-dechlorovancomycin) aglycon
    Evans, DA
    Barrow, JC
    Watson, PS
    Ratz, AM
    Dinsmore, CJ
    Evrard, DA
    DeVries, KM
    Ellman, JA
    Rychnovsky, SD
    Lacour, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (14) : 3419 - 3420
  • [13] THE 1ST TOTAL SYNTHESIS OF DEOXYBOUVARDIN AND RA-VII, NOVEL ANTITUMOR CYCLIC HEXAPEPTIDES
    INABA, T
    UMEZAWA, I
    YUASA, M
    INOUE, T
    MIHASHI, S
    ITOKAWA, H
    OGURA, K
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (13) : 2957 - 2958
  • [14] ANTITUMOR SUBSTANCES FROM HIGHER-PLANTS
    ITOKAWA, H
    TAKEYA, K
    [J]. HETEROCYCLES, 1993, 35 (02) : 1467 - 1501
  • [15] Total synthesis of the cyclic biphenyl ether peptides K-13 and OF4949-III via SNAr macrocyclization of peptidyl ruthenium pi-arene complexes
    Janetka, JW
    Rich, DH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (28) : 6488 - 6495
  • [16] Efficient synthesis of selectively protected L-Dopa derivatives from L-tyrosine via Reimer-Tiemann and Dakin reactions
    Jung, ME
    Lazarova, TI
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) : 1553 - 1555
  • [17] KONDA M, 1975, CHEM PHARM BULL, V23, P1063
  • [18] New synthetic technology for the synthesis of aryl ethers: Construction of C-O-D and D-O-E ring model systems of vancomycin
    Nicolaou, KC
    Boddy, CNC
    Natarajan, S
    Yue, TY
    Li, H
    Brase, S
    Ramanjulu, JM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (14) : 3421 - 3422
  • [19] Synthesis of an epimer of a 16-membered ring model for teicoplanin: Confirmation of epimerization during cycloamidation
    Pearson, AJ
    Zhang, PL
    Bignan, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (13) : 4536 - 4538
  • [20] Rao AVR, 1996, TETRAHEDRON LETT, V37, P3023