A formal total synthesis of deoxybouvardin

被引:22
作者
Bigot, A [1 ]
Beugelmans, R [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/S0040-4020(97)00706-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A synthesis of (L, L)-N, N-dimethylcycloisodityrosine 4 based on intramolecular SNAr reaction is reported. A possible explanation was proposed to account for the facile epimerization encountered in the cycloetherification of dipeptide (L,L)-10 and a solution to this problem led to a formal total synthesis of deoxybouvardin. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:10753 / 10764
页数:12
相关论文
共 56 条
  • [1] BATES RB, 1984, HETEROCYCLES, V22, P785
  • [2] SOLUTION FORMS OF BOUVARDIN AND RELATIVES FROM NMR-STUDIES - 6-O-METHYLBOUVARDIN
    BATES, RB
    COLE, JR
    HOFFMANN, JJ
    KRIEK, GR
    LINZ, GS
    TORRANCE, SJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (05) : 1343 - 1347
  • [3] THE FIRST EXAMPLES OF S(N)AR-BASED MACROCYCLIZATION - SYNTHESIS OF MODEL CARBOXYLATE-BINDING POCKETS OF VANCOMYCIN
    BEUGELMANS, R
    ZHU, JP
    HUSSON, N
    BOISCHOUSSY, M
    SINGH, GP
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (04) : 439 - 440
  • [4] A NOVEL SYNTHESIS OF K-13
    BEUGELMANS, R
    BIGOT, A
    ZHU, JP
    [J]. TETRAHEDRON LETTERS, 1994, 35 (40) : 7391 - 7394
  • [5] 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
  • [6] A NEW ACCESS TO 14-MEMBERED MACROCYCLE - SYNTHESIS OF MODEL F-O-G RING OF TEICOPLANIN
    BEUGELMANS, R
    BOURDET, S
    ZHU, JP
    [J]. TETRAHEDRON LETTERS, 1995, 36 (08) : 1279 - 1282
  • [7] THE FIRST SYNTHESIS OF A MODEL BICYCLIC D-O-E-F-O-G RING OF TEICOPLANIN VIA SEQUENTIAL INTRAMOLECULAR SNAR REACTIONS
    BEUGELMANS, R
    NEUVILLE, L
    BOISCHOUSSY, M
    ZHU, JP
    [J]. TETRAHEDRON LETTERS, 1995, 36 (48) : 8787 - 8790
  • [8] A new approach to the synthesis of piperazinomycin and bouvardin: Facile access to cycloisodityrosine via an intramolecular SNAr reaction
    Beugelmans, R
    Bigot, A
    BoisChoussy, M
    Zhu, JP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (02) : 771 - 774
  • [9] BEUGELMANS R, 1996, J CHEM SOC CHEM COMM, P1029
  • [10] Boger D L, 1994, Bioorg Med Chem, V2, P85, DOI 10.1016/S0968-0896(00)82005-2