IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v7y2016i1d10.1038_ncomms13852.html
   My bibliography  Save this article

Radical aryl migration enables diversity-oriented synthesis of structurally diverse medium/macro- or bridged-rings

Author

Listed:
  • Lei Li

    (South University of Science and Technology of China)

  • Zhong-Liang Li

    (South University of Science and Technology of China)

  • Fu-Li Wang

    (South University of Science and Technology of China)

  • Zhen Guo

    (College of Materials Science & Engineering, Taiyuan University of Technology)

  • Yong-Feng Cheng

    (South University of Science and Technology of China)

  • Na Wang

    (College of Materials Science & Engineering, Taiyuan University of Technology)

  • Xiao-Wu Dong

    (College of Pharmaceutical Sciences, Zhejiang University)

  • Chao Fang

    (South University of Science and Technology of China)

  • Jingjiang Liu

    (South University of Science and Technology of China)

  • Chunhui Hou

    (South University of Science and Technology of China)

  • Bin Tan

    (South University of Science and Technology of China)

  • Xin-Yuan Liu

    (South University of Science and Technology of China)

Abstract

Medium-sized and medium-bridged rings are attractive structural motifs in natural products and therapeutic agents. Due to the unfavourable entropic and/or enthalpic factors with these ring systems, their efficient construction remains a formidable challenge. To address this problem, we herein disclose a radical-based approach for diversity-oriented synthesis of various benzannulated carbon- and heteroatom-containing 8–11(14)-membered ketone libraries. This strategy involves 1,4- or 1,5-aryl migration triggered by radical azidation, trifluoromethylation, phosphonylation, sulfonylation, or perfluoroalkylation of unactivated alkenes followed by intramolecular ring expansion. Demonstration of this method as a highly flexible tool for the construction of 37 synthetically challenging medium-sized and macrocyclic ring scaffolds including bridged rings with diverse functionalities and skeletons is highlighted. Some of these products showed potent inhibitory activity against the cancer cell or derivative of human embryonic kidney line in preliminary biological studies. The mechanism of this novel strategy is investigated by control experiments and DFT calculations.

Suggested Citation

  • Lei Li & Zhong-Liang Li & Fu-Li Wang & Zhen Guo & Yong-Feng Cheng & Na Wang & Xiao-Wu Dong & Chao Fang & Jingjiang Liu & Chunhui Hou & Bin Tan & Xin-Yuan Liu, 2016. "Radical aryl migration enables diversity-oriented synthesis of structurally diverse medium/macro- or bridged-rings," Nature Communications, Nature, vol. 7(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:7:y:2016:i:1:d:10.1038_ncomms13852
    DOI: 10.1038/ncomms13852
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/ncomms13852
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/ncomms13852?utm_source=ideas
    LibKey link: if access is restricted and if your library uses this service, LibKey will redirect you to where you can use your library subscription to access this item
    ---><---

    Citations

    Citations are extracted by the CitEc Project, subscribe to its RSS feed for this item.
    as


    Cited by:

    1. Jingpeng Han & Yongjian Yang & Yingjian Gong & Xuan Tang & Yi Tian & Baosheng Li, 2023. "Divergent access to 5,6,7-perifused cycles," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
    2. Jiapian Huang & Fei Liu & Ling-Hui Zeng & Shaoyu Li & Zhiyuan Chen & Jie Wu, 2022. "Accessing chiral sulfones bearing quaternary carbon stereocenters via photoinduced radical sulfur dioxide insertion and Truce–Smiles rearrangement," Nature Communications, Nature, vol. 13(1), pages 1-9, December.

    More about this item

    Statistics

    Access and download statistics

    Corrections

    All material on this site has been provided by the respective publishers and authors. You can help correct errors and omissions. When requesting a correction, please mention this item's handle: RePEc:nat:natcom:v:7:y:2016:i:1:d:10.1038_ncomms13852. See general information about how to correct material in RePEc.

    If you have authored this item and are not yet registered with RePEc, we encourage you to do it here. This allows to link your profile to this item. It also allows you to accept potential citations to this item that we are uncertain about.

    We have no bibliographic references for this item. You can help adding them by using this form .

    If you know of missing items citing this one, you can help us creating those links by adding the relevant references in the same way as above, for each refering item. If you are a registered author of this item, you may also want to check the "citations" tab in your RePEc Author Service profile, as there may be some citations waiting for confirmation.

    For technical questions regarding this item, or to correct its authors, title, abstract, bibliographic or download information, contact: Sonal Shukla or Springer Nature Abstracting and Indexing (email available below). General contact details of provider: http://www.nature.com .

    Please note that corrections may take a couple of weeks to filter through the various RePEc services.

    IDEAS is a RePEc service. RePEc uses bibliographic data supplied by the respective publishers.