Facile construction of the colchicine skeleton by a rhodium-catalyzed cyclization cycloaddition cascade

被引:0
|
作者
Graening, T
Friedrichsen, W
Lex, J
Schmalz, HG
机构
[1] Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany
[2] Univ Kiel, Inst Organ Chem, D-24098 Kiel, Germany
关键词
D O I
10.1002/1521-3773(20020503)41:9<1524::AID-ANIE1524>3.0.CO;2-9
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The major alkaloid of the meadow saffron is colchicine, which displays remarkable antimitotic activity and has long been used in the treatment of acute gout and is currently being tested against a broad variety of other diseases. In a remarkable Rh-catalyzed domino transformation, the complete carbon skeleton of this important alkaloid is assembled with high efficiency (see scheme). TBS = tert-butyldimethylsilyl, TMS = trimethylsilyl.
引用
收藏
页码:1524 / 1526
页数:3
相关论文
共 50 条
  • [21] Rhodium-Catalyzed Enantioselective Cyclization of 2-Allenylbenzoxazoles
    Becker, Antonia
    Bauer, Felix
    Breit, Bernhard
    ORGANIC LETTERS, 2024, 26 (12) : 2451 - 2455
  • [22] Divergent Rhodium-Catalyzed Cyclization Reactions of Enoldiazoacetamides with Nitrosoarenes
    Cheng, Qing-Qing
    Lankelma, Marianne
    Wherritt, Daniel
    Arman, Hadi
    Doyle, Michael P.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (29) : 9839 - 9842
  • [23] Synthesis of Indene Frameworks via Rhodium-Catalyzed Cascade Cyclization of Aromatic Ketone and Unsaturated Carbonyl Compounds
    Shi, Xian-Ying
    Li, Chao-Jun
    ORGANIC LETTERS, 2013, 15 (07) : 1476 - 1479
  • [24] Facile Synthesis of Dibenzotetracenedione Derivatives by Rhodium-Catalyzed [2+2+2] Cycloaddition/Spontaneous Aromatization
    Aida, Yukimasa
    Shibata, Yu
    Tanaka, Ken
    CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (10) : 1823 - 1829
  • [25] Single-Step Construction of Planar and Central Chirality in Metallocenes by Rhodium-Catalyzed Desymmetric Cyclization
    Yang, Ying
    Hang, Nan-Nan
    Liu, Hui-Yao
    Chen, Shufeng
    Ming, Jialin
    ACS CATALYSIS, 2023, 13 (19) : 12464 - 12471
  • [26] Rhodium-catalyzed cascade reaction of 1,6-enynes involving addition, cyclization, and β-oxygen elimination
    Miura, Tomoya
    Shimada, Masahiko
    Murakami, Masahiro
    CHEMISTRY-AN ASIAN JOURNAL, 2006, 1 (06) : 868 - 877
  • [27] Triptycenediols by Rhodium-Catalyzed [2+2+2] Cycloaddition
    Taylor, Mark S.
    Swager, Timothy M.
    ORGANIC LETTERS, 2007, 9 (18) : 3695 - 3697
  • [28] Rhodium-Catalyzed [2+2] Cycloaddition of Ynamides with Nitroalkenes
    Smith, Donna L.
    Chidipudi, Suresh Reddy
    Goundry, William R.
    Lam, Hon Wai
    ORGANIC LETTERS, 2012, 14 (18) : 4934 - 4937
  • [29] Rhodium-catalyzed [5+2] cycloaddition reactions in water
    Wender, PA
    Love, JA
    Williams, TJ
    SYNLETT, 2003, (09) : 1295 - 1298
  • [30] Asymmetric synthesis of tropanes by rhodium-catalyzed [4 + 3] cycloaddition
    Reddy, Ravisekhara P.
    Davies, Huw M. L.
    Journal of the American Chemical Society, 2007, 129 (34): : 10312 - 10313