Studies towards the total synthesis of batzelladine A

被引:48
|
作者
Elliott, MC [1 ]
Long, MS [1 ]
机构
[1] Cardiff Univ, Sch Chem, Cardiff CF10 3TB, S Glam, Wales
关键词
D O I
10.1039/b404679j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Application of a diastereoselective three-component coupling to the bicyclic core of the batzelladine alkaloids is described. The synthesis features the elaboration of glutamic acid by use of Eschenmoser sulfide contraction. An earlier approach is also included, which shows some limitations of dithiane chemistry when applied to the particular compounds required for this target.
引用
收藏
页码:2003 / 2011
页数:9
相关论文
共 50 条
  • [1] Studies towards the total synthesis of Batzelladine A:: synthesis of a model pyrrolo[1,2-c]pyrimidine
    Elliott, MC
    Long, MS
    TETRAHEDRON LETTERS, 2002, 43 (50) : 9191 - 9194
  • [2] Enantioselective total synthesis of batzelladine A
    Shimokawa, J
    Shirai, K
    Tanatani, A
    Hashimoto, Y
    Nagasawa, K
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) : 1559 - 1562
  • [3] Total synthesis of (+)-batzelladine A and (-)-batzelladine D, and identification of their target protein
    Shimokawa, J
    Ishiwata, T
    Shirai, K
    Koshino, H
    Tanatani, A
    Nakata, T
    Hashimoto, Y
    Nagasawa, K
    CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (23) : 6878 - 6888
  • [4] Total synthesis of batzelladine D
    Ishiwata, T
    Hino, T
    Koshino, H
    Hashimoto, Y
    Nakata, T
    Nagasawa, K
    ORGANIC LETTERS, 2002, 4 (17) : 2921 - 2924
  • [5] Asymmetric total synthesis of batzelladine D
    Cohen, F
    Overman, LE
    Sakata, SKL
    ORGANIC LETTERS, 1999, 1 (13) : 2169 - 2172
  • [6] Total Synthesis of (±)-Batzelladine K: A Biomimetic Approach
    Ahmed, Nafees
    Brahmbhatt, Keyur G.
    Singh, Inder Pal
    Bhutani, Kamlesh K.
    SYNTHESIS-STUTTGART, 2010, (15): : 2567 - 2570
  • [7] An approach to the total synthesis of batzelladine A utilizing a tethered Biginelli condensation
    Franklin, AS
    Overman, LE
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 212 : 319 - ORGN
  • [8] Enantioselective total synthesis of batzelladine F and definition of its structure
    Cohen, F
    Overman, LE
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) : 2604 - 2608
  • [9] Evolution of a strategy for the synthesis of structurally complex batzelladine alkaloids. Enantioselective total synthesis of the proposed structure of batzelladine F and structural revision
    Cohen, Frederick
    Overman, Larry E.
    Journal of the American Chemical Society, 2006, 128 (08): : 2594 - 2603
  • [10] Studies towards the total synthesis of anguidine
    Yingzhao, David
    Manetsch, Roman
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258