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
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
  • [21] Total synthesis of the putative structure of the marine alkaloid haliclorensin
    Banwell, MG
    Bray, AM
    Edwards, AJ
    Wong, DJ
    NEW JOURNAL OF CHEMISTRY, 2001, 25 (11) : 1347 - 1350
  • [22] Total Synthesis of the Marine Bromotyrosine Alkaloid Moloka'iakitamide
    Yoshida, Makoto
    Yamaguchi, Kentaro
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2009, 57 (10) : 1147 - 1149
  • [23] Total Synthesis of Marine Alkaloid Hyellazole and its Derivatives
    Chakraborty, Suchandra
    Saha, Chandan
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (17) : 2013 - 2021
  • [24] Enantioselective total synthesis of the marine alkaloid lepadin B
    Toyooka, N
    Okumura, M
    Takahata, H
    JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07): : 2182 - 2183
  • [25] Studies on total synthesis of the cytotoxic marine alkaloid agelastatin A
    Anderson, GT
    Chase, CE
    Koh, YH
    Stien, D
    Weinreb, SM
    Shang, MY
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22): : 7594 - 7595
  • [26] Total Synthesis of a Marine Alkaloid-Rigidin E
    Cao, Banpeng
    Ding, Haixin
    Yang, Ruchun
    Wang, Xiaoji
    Xiao, Qiang
    MARINE DRUGS, 2012, 10 (06): : 1412 - 1421
  • [27] Total synthesis of the antitumor marine sponge alkaloid agelastatin A
    Stien, D
    Anderson, GT
    Chase, CE
    Koh, Y
    Weinreb, SM
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (41) : 9574 - 9579
  • [28] A new total synthesis of the marine tunicate alkaloid lepadiformine
    Sun, P
    Sun, CX
    Weinreb, SM
    ORGANIC LETTERS, 2001, 3 (22) : 3507 - 3510
  • [29] Explorations on the total synthesis of the unusual marine alkaloid chartelline A
    Sun, CX
    Lin, XC
    Weinreb, SM
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (08): : 3159 - 3166
  • [30] Enentioselective Total Synthesis of the Marine Alkaloid Clavepictines A and B
    Toyooka, N.
    Yotsui, Y.
    Yoshida, Y.
    Momose, T.
    Journal of Organic Chemistry, 61 (15):