Regioselective acylation at the 5-or 6-position of L-tryptophan derivatives

被引:6
作者
Jiang, YW
Ma, DW [1 ]
机构
[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1016/S0040-4039(02)01580-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of 1-acyl tryptophan derivatives with chloroacetyl chloride or the reaction of 1-tosyl tryptophan derivatives with acetyl chloride provides the corresponding 6-acylation products, while acylation of the 3-oxo tryptophan derivative gives a 5-substituted product. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7013 / 7015
页数:3
相关论文
共 18 条
  • [1] A concise, efficient route to fumitremorgins
    Bailey, PD
    Cochrane, PJ
    Lorenz, K
    Collier, ID
    Pearson, DPJ
    Rosair, GM
    [J]. TETRAHEDRON LETTERS, 2001, 42 (01) : 113 - 115
  • [2] Regioselective acylations at the 2 and 6 position of N-acetylindole
    Cruz, RPA
    Ottoni, O
    Abella, CAM
    Aquino, LB
    [J]. TETRAHEDRON LETTERS, 2001, 42 (08) : 1467 - 1469
  • [3] Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus .2. Physico-chemical properties and structures
    Cui, CB
    Kakeya, H
    Osada, H
    [J]. JOURNAL OF ANTIBIOTICS, 1996, 49 (06) : 534 - 540
  • [4] Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus .1. Taxonomy, fermentation, isolation and biological properties
    Cui, CB
    Kakeya, H
    Okada, G
    Onose, R
    Osada, H
    [J]. JOURNAL OF ANTIBIOTICS, 1996, 49 (06) : 527 - 533
  • [5] TRYPROSTATIN-A AND TRYPROSTATIN-B, NOVEL MAMMALIAN-CELL CYCLE INHIBITORS PRODUCED BY ASPERGILLUS-FUMIGATUS
    CUI, CB
    KAKEYA, H
    OKADA, G
    ONOSE, R
    UBUKATA, M
    TAKAHASHI, I
    ISONO, K
    OSADA, H
    [J]. JOURNAL OF ANTIBIOTICS, 1995, 48 (11) : 1382 - 1384
  • [6] Edmondson SD, 1998, ANGEW CHEM INT EDIT, V37, P1138, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1138::AID-ANIE1138>3.0.CO
  • [7] 2-N
  • [8] Guo YP, 1999, CANCER RES, V59, P1366
  • [9] Modeling chemistry, and biology of the benzolactam analogues of indolactam V (ILV) .2. Identification of the binding site of the benzolactams in the CRD2 activator-binding domain of PKC delta and discovery of an ILV analogue of improved isozyme selectivity
    Kozikowski, AP
    Wang, SM
    Ma, DW
    Yao, JC
    Ahmad, S
    Glazer, RI
    Bogi, K
    Acs, P
    Modarres, S
    Lewin, NE
    Blumberg, PM
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (09) : 1316 - 1326
  • [10] Stereospecific synthesis of 9-substituted benzolactam-V8 from L-tyrosine via regioselective aromatic nitration
    Ma, DW
    Tang, WJ
    [J]. TETRAHEDRON LETTERS, 1998, 39 (40) : 7369 - 7372