Total synthesis of a marine imidazole alkaloid, clathridine A

被引：20
|
作者：
Ohta, S [1 ]
Tsuno, N [1 ]
Maeda, K [1 ]
Nakamura, S [1 ]
Taguchi, N [1 ]
Yamashita, M [1 ]
Kawasaki, I [1 ]
机构：
[1] Kyoto Pharmaceut Univ, Kyoto 6078414, Japan
来源：
TETRAHEDRON LETTERS | 2000年 / 41卷 / 23期
关键词：
clathridine A; preclathridine A; marine alkaloid; total synthesis; parabanic acid; regioselective condensation; imidazole;
D O I：
10.1016/S0040-4039(00)00678-X
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The first total synthesis of clathridine A (8), a marine imidazole alkaloid, was achieved by using a novel regioselective condensation as a key step, in which preclathridine A (2) was treated with 1-methylparabanic acid (11) in the presence of a silylating agent. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：4623 / 4627
页数：5
相关论文
共 50 条
  • [41] Total synthesis of marine bisindole alkaloid (+)-cis-dihydrohamacanthin B
    Higuchi, Kazuhiro
    Takei, Ryousuke
    Kouko, Takashi
    Kawasaki, Tomomi
    SYNTHESIS-STUTTGART, 2007, (05): : 669 - 674
  • [42] Construction of an advanced tetracyclic intermediate for total synthesis of the marine alkaloid sarain A
    Hong, SW
    Yang, JH
    Weinreb, SM
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (05): : 2078 - 2089
  • [43] A Total Synthesis of the Marine Alkaloid Ningalin B from (S)-Proline
    Hasse, Katrin
    Willis, Anthony C.
    Banwell, Martin G.
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2009, 62 (07) : 683 - 691
  • [44] TOTAL SYNTHESIS OF (+/-)-DRAGMACIDIN - A CYTOTOXIC BIS(INDOLE)ALKALOID OF MARINE ORIGIN
    JIANG, B
    SMALLHEER, JM
    AMARALLY, C
    WUONOLA, MA
    JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (22): : 6823 - 6827
  • [45] Evolution of a Strategy for Total Synthesis of the Marine Fungal Alkaloid (±)-Communesin F
    Seo, Jae Hong
    Liu, Peng
    Weinreb, Steven M.
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (08): : 2667 - 2680
  • [46] The first total synthesis of veiutamine, a new type of pyrroloiminoquinone marine alkaloid
    Moro-oka, Y
    Fukuda, T
    Iwao, M
    TETRAHEDRON LETTERS, 1999, 40 (09) : 1713 - 1716
  • [47] Total synthesis and bioactivity of the marine alkaloid pityriacitrin and some of its derivatives
    Zhang, Puyong
    Sun, Xiaofei
    Xu, Bin
    Bijian, Krikor
    Wan, Shengbiao
    Li, Guigen
    Alaoui-Jamali, Moulay
    Jiang, Tao
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (12) : 6089 - 6097
  • [48] Total synthesis of naamine C and pyronaamidine, antitumor marine imidazole alkaloids
    Nakamura, S
    Kawasaki, I
    Kunimura, M
    Matsui, M
    Noma, Y
    Yamashita, M
    Ohta, S
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (08): : 1061 - 1066
  • [49] Expedient total syntheses of preclathridine A and clathridine A
    Koswatta, Panduka B.
    Lovely, Carl J.
    TETRAHEDRON LETTERS, 2009, 50 (35) : 4998 - 5000
  • [50] Synthesis of the marine alkaloid caulersin
    Wahlström, N
    Stensland, B
    Bergman, J
    TETRAHEDRON, 2004, 60 (09) : 2147 - 2153
12345