Woodward's unfinished total synthesis of colchicine, a collaborative prelude

被引:2
作者
Sigg, Hans-Peter [1 ]
Hendrickson, James B. [2 ]
Craig, G. Wayne [3 ]
机构
[1] Sandoz AG, CH-4104 Oberwil, Switzerland
[2] Brandeis Univ, Dept Chem, Waltham, MA 02254 USA
[3] Syncoba GmbH, Lead Finding Res, CH-4144 Arlesheim, Switzerland
关键词
History of chemistry; Robert B. Woodward; Albert Eschenmoser; Total synthesis; Colchicine; Vitamin B-12;
D O I
10.1016/j.tet.2016.05.051
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This article describes Robert B. Woodward's unfinished total synthesis of colchicine and the strategy that required a brilliant new beginning in 1959. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5563 / 5576
页数:14
相关论文
共 50 条
  • [1] R. B. Woodward's unfinished symphony: designing organic superconductors (1975-79)
    Cava, Michael P.
    Lakshmikantham, M. V.
    Hoffmann, Roald
    Williams, Robert M.
    TETRAHEDRON, 2011, 67 (36) : 6771 - 6797
  • [2] Total synthesis of (-)-colchicine by an oxyallyl [4+3] cycloaddition
    Lee, JC
    Cha, JK
    TETRAHEDRON, 2000, 56 (52) : 10175 - 10184
  • [3] The Woodward-Doering/Rabe-Kindler total synthesis of quinine: Setting the record straight
    Seeman, Jeffrey I.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (09) : 1378 - 1413
  • [4] Total synthesis of (+)-blasticidin S
    Ichikawa, Y
    Hirata, K
    Ohbayashi, M
    Isobe, M
    CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (13) : 3241 - 3251
  • [5] Total synthesis of selaginellin S
    Fujiwara, Kenshu
    Itagaki, Takaya
    Kondo, Yoshihiko
    Akiba, Uichi
    Tokiwano, Tetsuo
    TETRAHEDRON LETTERS, 2020, 61 (25)
  • [6] Enantioselective total synthesis of (-)-colchicine, (+)-demecolcinone and metacolchicine: determination of the absolute configurations of the latter two alkaloids
    Chen, Bo
    Liu, Xin
    Hu, Ya-Jian
    Zhang, Dong-Mei
    Deng, Lijuan
    Lu, Jieyu
    Min, Long
    Ye, Wen-Cai
    Li, Chuang-Chuang
    CHEMICAL SCIENCE, 2017, 8 (07) : 4961 - 4966
  • [7] Total Synthesis of (±)-Carquinostatin A, and Asymmetric Total Synthesis of (R)-(-)-Carquinostatin A and (S)-(+)-Carquinostatin A
    Hieda, Yuhzo
    Choshi, Tominari
    Uchida, Yoshinari
    Fujioka, Haruto
    Fujii, Sayuri
    Hibino, Satoshi
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2012, 60 (12) : 1522 - 1530
  • [8] Total synthesis of (S)-(+)-curcudiol, and (S)-(+)- and (R)-(-)-curcuphenol
    Ono, M
    Ogura, Y
    Hatogai, K
    Akita, H
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2001, 49 (12) : 1581 - 1585
  • [9] Synthesis of conjugates of (aR,7S)-colchicine with monoterpenoids and investigation of their biological activity
    E. S. Shchegravina
    S. D. Usova
    D. S. Baev
    E. S. Mozhaitsev
    D. N. Shcherbakov
    S. V. Belenkaya
    E. A. Volosnikova
    V. Yu. Chirkova
    E. A. Sharlaeva
    E. V. Svirshchevskaya
    I. P. Fonareva
    A. R. Sitdikova
    N. F. Salakhutdinov
    O. I. Yarovaya
    A. Yu. Fedorov
    Russian Chemical Bulletin, 2023, 72 : 248 - 262
  • [10] Synthesis of conjugates of (aR,7S)-colchicine with monoterpenoids and investigation of their biological activity
    Shchegravina, E. S.
    Usova, S. D.
    Baev, D. S.
    Mozhaitsev, E. S.
    Shcherbakov, D. N.
    Belenkaya, S. V.
    Volosnikova, E. A.
    Chirkova, V. Yu.
    Sharlaeva, E. A.
    Svirshchevskaya, E. V.
    Fonareva, I. P.
    Sitdikova, A. R.
    Salakhutdinov, N. F.
    Yarovaya, O. I.
    Fedorov, A. Yu.
    RUSSIAN CHEMICAL BULLETIN, 2023, 72 (01) : 248 - 262