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
  • [1] Synthesis of kainoids via a highly stereoselective hydroformylation of kainic acid
    Rodriquez, M
    Bassarello, C
    Bifulco, G
    Gomez-Paloma, L
    Mann, A
    Marchetti, M
    Schoenfelder, A
    Taddei, M
    SYNLETT, 2005, (10) : 1581 - 1585
  • [2] A NEW ENANTIOSELECTIVE ROUTE TO KAINOIDS - APPLICATION TO THE FORMAL SYNTHESIS OF (-)-ALPHA-KAINIC ACID
    BARCO, A
    BENETTI, S
    POLLINI, GP
    SPALLUTO, G
    ZANIRATO, V
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (06) : 390 - 391
  • [3] Efficient synthesis of kainic acid analogues
    Tamborini, Lucia
    Mastronardi, Federica
    Cullia, Gregorio
    Ettari, Roberta
    De Micheli, Carlo
    ARKIVOC, 2013, : 377 - 387
  • [4] Overview of the synthetic routes to tadalafil and its analogues
    Gouda, Moustafa A.
    SYNTHETIC COMMUNICATIONS, 2017, 47 (24) : 2269 - 2304
  • [5] Overview of the synthetic routes to sildenafil and its analogues
    Gouda, Moustafa A.
    Hamama, Wafaa S.
    SYNTHETIC COMMUNICATIONS, 2017, 47 (14) : 1269 - 1300
  • [6] New Synthetic Routes to Acronycine, Noracronycine, and Their Analogues
    Hari, Galla Sri
    Lee, Yong Rok
    Wang, Xue
    Lyoo, Won Seok
    Kim, Sung Hong
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2010, 31 (08): : 2406 - 2409
  • [7] Novel approach to the (-)-sparteine-mediated synthesis of kainoids:: Total synthesis of (-)-α-kainic acid by (-)-sparteine-mediated deprotonation
    Martínez, MM
    Hoppe, D
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (07) : 1427 - 1443
  • [8] New synthetic routes to the phosphonate analogues of nucleotides.
    Brel, VK
    Stang, PJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U559 - U559
  • [9] Parallel synthesis of novel heteroaromatic acromelic acid analogues from kainic acid
    Baldwin, JE
    Fryer, AM
    Pritchard, GJ
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (08): : 2588 - 2596
  • [10] A NEW APPROACH TO KAINOIDS THROUGH TANDEM MICHAEL REACTION METHODOLOGY - APPLICATION TO THE ENANTIOSELECTIVE SYNTHESIS OF (+)-ALPHA-ALLOKAINIC AND (-)-ALPHA-ALLOKAINIC ACID AND TO THE FORMAL SYNTHESIS OF (-)-ALPHA-KAINIC ACID
    BARCO, A
    BENETTI, S
    SPALLUTO, G
    CASOLARI, A
    POLLINI, GP
    ZANIRATO, V
    JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23): : 6279 - 6286
12345