Concise and Diversity-Oriented Route toward Polysubstituted 2-Aminoimidazole Alkaloids and Their Analogues

被引：142
|
作者：
Ermolat'ev, Denis S. [1 ]
Bariwal, Jitender B. [1 ]
Steenackers, Hans P. L. [2 ]
De Keersmaecker, Sigrid C. J. [2 ]
Van der Eycken, Erik V. [1 ]
机构：
[1] Katholieke Univ Leuven, Lab Organ & Microwave Assisted Chem, B-3001 Louvain, Belgium
[2] Katholieke Univ Leuven, Ctr Microbial & Plant Genet, B-3001 Louvain, Belgium
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 49期
关键词：
alkaloids; 2-aminoimidazoles; cyclization; heterocycles; natural products; MICROWAVE-ASSISTED SYNTHESIS; HOMOGENEOUS GOLD CATALYSIS; IMIDAZOLE ALKALOIDS; HYDROAMINATION; HETEROCYCLES; CARBOCYCLES; ALKENES; ALKYNES; LIBRARY;
D O I：
10.1002/anie.201004256
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Alkaloids of the naamine family were synthesized from diverse propargylamines in just two steps (see scheme: R1=Me, R 2=substituted benzyl, R3=Ar). Thus, the addition to a propargylamine of a carbodiimide generated in situ, silver(I)-catalyzed intramolecular hydroamidation, and subsquent deprotection provide access to the heterocyclic core of numerous natural products and biologically active compounds. Boc=tert-butoxycarbonyl, Cbz=carbobenzyloxy. Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：9465 / 9468
页数：4
相关论文
共 50 条
  • [41] A Diversity-Oriented Synthesis of Bicyclic cis-Dihydroarenediols, cis-4-Hydroxyscytalones, and Bicyclic Conduritol Analogues
    Mukherjee, Parag
    Roy, Soumya J. Singha
    Sarkar, Tarun K.
    ORGANIC LETTERS, 2010, 12 (11) : 2472 - 2475
  • [42] Diversity-oriented synthesis of analogues of the novel macrocyclic peptide FR-225497 through late stage functionalization
    Mukherjee, Jyotiprasad
    Sil, Suman
    Chattopadhyay, Shital Kumar
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 2487 - 2492
  • [43] A Diversity-Oriented Strategy for Chemical Synthesis of Glycosphingolipids: Synthesis of Glycosphingolipid LcGg4 and Its Analogues and Derivatives
    Rohokale, Rajendra S.
    Li, Qingjiang
    Guo, Zhongwu
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (02): : 1633 - 1648
  • [44] Biology- and Diversity-Oriented Domino Reactions for Synthesis of AMPA Receptor Antagonist IKM-159 and Analogues
    Oikawa, Masato
    Kasori, Yuuki
    Katayama, Lisa
    Murakami, Etsuko
    Oikawa, Yuya
    Ishikawa, Yuichi
    SYNTHESIS-STUTTGART, 2013, 45 (22): : 3106 - 3117
  • [45] Diversity-Oriented Synthesis of Substituted Furo[2,3-b]pyrazines
    Mehta, Vaibhav P.
    Modha, Sachin G.
    Ermolat'ev, Denis
    Van Hecke, Kristof
    Van Meervelt, Luc
    Van der Eycken, Erik V.
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2009, 62 (01) : 27 - 41
  • [46] Diversity-Oriented Silver(I)-Mediated Synthesis of Spiro-2-aminoimidazoles
    Pereshivko, Olga P.
    Peshkov, Vsevolod A.
    Ermolat'ev, Denis S.
    Van Hove, Sofie
    Van Hecke, Kristof
    Van Meervelt, Luc
    Van der Eycken, Erik V.
    SYNTHESIS-STUTTGART, 2011, (10): : 1587 - 1594
  • [47] Stereodivergent Diversity-Oriented Synthesis: Exploiting the Versatility of 2-Piperidine Ethanol
    Bonandi, Elisa
    Marzullo, Paola
    Foschi, Francesca
    Perdicchia, Dario
    Lo Presti, Leonardo
    Sironi, Maurizio
    Pieraccini, Stefano
    Gambacorta, Guido
    Saupe, Joern
    Dalla Via, Lisa
    Passarella, Daniele
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (25) : 4013 - 4019
  • [48] Diastereoselective 2-aza-Cope rearrangements and their applications in diversity-oriented synthesis
    Ibbeson, Brett M.
    Blackwell, David T.
    Spring, David R.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [49] Toward the library generation of natural product-like polycyclic derivatives by stereocontrolled diversity-oriented synthesis
    Arya, R
    Quevillon, S
    Joseph, R
    Wei, CQ
    Gan, Z
    Parisien, M
    Sesmilo, E
    Reddy, RT
    Chen, ZX
    Durieux, R
    Laforce, D
    Campeau, LC
    Khadem, S
    Couve-Bonnaire, S
    Kumar, R
    Sharma, U
    Leek, DM
    Daroszewska, M
    Barnes, ML
    PURE AND APPLIED CHEMISTRY, 2005, 77 (01) : 163 - 178
  • [50] A Concise and Diversity-Oriented Strategy for the Synthesis of Substituted 2-Pyrrolidinones via an Ugi/Intramolecular Inverse Electron Demand Diels-Alder Sequence
    Liu, Yan
    Shang, Tianyi
    Chen, Zhong
    Zhang, Yaozhou
    Sun, Wei
    Yang, Junjie
    Pan, Yan
    ADVANCES IN APPLIED BIOTECHNOLOGY, 2018, 444 : 413 - 419
12345