New synthetic routes to the kainoids: a synthesis of kainic acid and its analogues

被引:11
|
作者
Parsons, Philip J. [1 ]
Rushton, Stephen P. G. [1 ]
Panta, Raghava R. [1 ]
Murray, Adrian J. [1 ]
Coles, Martyn P. [1 ]
Lai, Jason [1 ]
机构
[1] Univ Sussex, Sch Life Sci, Dept Chem, Brighton BN1 9QJ, E Sussex, England
关键词
Excitatory amino acids; Nitrile oxide; Kainate; Ene-reaction; Isoxazolidinone; ENANTIOSELECTIVE TOTAL-SYNTHESIS; (-)-KAINIC ACID; (-)-ALPHA-KAINIC ACID; (+)-ALPHA-ALLOKAINIC ACID; CYCLIZATION; INSERTION;
D O I
10.1016/j.tet.2011.10.030
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New approaches to the synthesis of kainic acid and its analogues are presented. Two distinctly different approaches are described; the former utilised an intermolecular nitrile oxide addition to a homochiral substrate to furnish epikainate models and the second utilised amino acid chemistry to secure kainic acid. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:10267 / 10273
页数:7
相关论文
共 50 条
  • [21] Chemical synthesis of shikimic acid and its analogues
    Jiang, SD
    Singh, G
    TETRAHEDRON, 1998, 54 (19) : 4697 - 4753
  • [22] NEW SYNTHETIC ROUTES TO TILORONE DIHYDROCHLORIDE AND SOME OF ITS ANALOGS
    BURKE, HM
    JOULLIE, MM
    JOURNAL OF MEDICINAL CHEMISTRY, 1978, 21 (10) : 1084 - 1086
  • [24] A Practical Synthesis of (-)-Kainic Acid
    Takita, Satoshi
    Yokoshima, Satoshi
    Fukuyama, Tohru
    SYNTHESIS-STUTTGART, 2011, (23): : 3848 - 3858
  • [25] Synthetic studies directed toward kainic acid
    Lu, JH
    Matteson, DS
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 211 : 221 - ORGN
  • [26] Approaches to a synthesis of α-kainic acid
    Cossy, J
    Cases, M
    Pardo, DG
    TETRAHEDRON, 1999, 55 (19) : 6153 - 6166
  • [27] PROGRESS IN THE SYNTHESIS OF (-)-α-KAINIC ACID
    Choony, Nandeo
    James, Lisa
    Rabun, Courtney
    SYNTHETIC COMMUNICATIONS, 2011, 41 (17) : 2539 - 2543
  • [28] Practical synthesis of (-)-kainic acid
    Takita, Satoshi
    Yokoshima, Satoshi
    Fukuyama, Tohru
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
  • [29] NEW SYNTHETIC ROUTES TO SYNTHONS FOR SYNTHESIS OF FUNCTIONALIZED ASPIDOSPERMA ALKALOIDS
    TAKANO, S
    SHISHIDO, K
    SATO, M
    YUTA, K
    OGASAWARA, K
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (21) : 943 - 944
  • [30] Design and synthesis of conformationally constrained analogues of kainic acid as ionotroplic glutamate receptor ligands.
    Shou, XH
    Chamberlin, AR
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U32 - U32