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
来源：
TETRAHEDRON | 2011年 / 67卷 / 52期
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
  • [31] Synthesis of excitatory amino acid analogues
    Goundry, William R. F.
    Lee, Victor
    Baldwin, Jack E.
    SYNLETT, 2006, (15) : 2407 - 2410
  • [32] Kainic acid: its tritiation revisited with added technical details
    Crist N. Filer
    Richard J. Seguin
    Journal of Radioanalytical and Nuclear Chemistry, 2020, 324 : 423 - 428
  • [33] Total Synthesis of Cryptopleurine and Its Analogues
    Yamaoka, Yousuke
    Yamakawa, Takuro
    Tateishi, Kaito
    Takasu, Kiyosei
    SYNTHESIS-STUTTGART, 2022, 54 (10): : 2415 - 2422
  • [34] Synthesis of (+)-Centrolobine and Its Analogues by Using Acyl Anion Chemistry
    Sudarshan, Kasireddy
    Aidhen, Indrapal Singh
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (12) : 2298 - 2302
  • [35] Total Synthesis of (-)-α-Kainic acid via Chirality Transfer through Ireland-Claisen Rearrangement
    Reddy, Naredla Kesava
    Chandrasekhar, Srivari
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (07) : 3355 - 3360
  • [36] Diastereoselective Rhodium-Catalyzed Ene-Cycloisomerization Reactions of Alkenylidenecyclopropanes: Total Synthesis of (-)-α-Kainic Acid
    Evans, P. Andrew
    Inglesby, Phillip A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (08) : 3635 - 3638
  • [37] Palladium-Mediated Annulation of Vinyl Aziridines with Michael Acceptors: Stereocontrolled Synthesis of Substituted Pyrrolidines and Its Application in a Formal Synthesis of (-)-α-Kainic Acid
    Lowe, Martin A.
    Ostovar, Mehrnoosh
    Ferrini, Serena
    Chen, C. Chun
    Lawrence, Paul G.
    Fontana, Francesco
    Calabrese, Andrew A.
    Aggarwal, Varinder K.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (28) : 6370 - 6374
  • [38] Comparison of the in vitro and in vivo neurotoxicity of three new sources of kainic acid
    Tasker, RAR
    Bernard, PB
    Doucette, TA
    Kerr, DS
    Zabidin, Y
    Alvarez-Fernandez, L
    Fernandez-Maroto, B
    Fernandez-Sanchez, MT
    Novelli, A
    AMINO ACIDS, 2002, 23 (1-3) : 45 - 54
  • [39] Comparison of the in vitro and in vivo neurotoxicity of three new sources of kainic acid
    R. A. R. Tasker
    P. B. Bernard
    T. A. Doucette
    D. S. Kerr
    Y. Zabidin
    L. Alvarez-Fernandez
    B. Fernandez-Maroto
    M. T. Fernandez-Sanchez
    A. Novelli
    Amino Acids, 2002, 23 : 45 - 54
  • [40] Extragonadal synthesis of estradiol is protective against kainic acid excitotoxic damage to the hippocampus
    Veiga, S
    Azcoitia, I
    Garcia-Segura, LM
    NEUROREPORT, 2005, 16 (14) : 1599 - 1603
12345