IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v7y2016i1d10.1038_ncomms12183.html
   My bibliography  Save this article

Total synthesis of atropurpuran

Author

Listed:
  • Jing Gong

    (Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, Sichuan University, No. 17, Section 3, Renmin Nan Road, Chengdu 610041, China)

  • Huan Chen

    (Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, Sichuan University, No. 17, Section 3, Renmin Nan Road, Chengdu 610041, China)

  • Xiao-Yu Liu

    (Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, Sichuan University, No. 17, Section 3, Renmin Nan Road, Chengdu 610041, China)

  • Zhi-Xiu Wang

    (Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, Sichuan University, No. 17, Section 3, Renmin Nan Road, Chengdu 610041, China)

  • Wei Nie

    (Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, Sichuan University, No. 17, Section 3, Renmin Nan Road, Chengdu 610041, China)

  • Yong Qin

    (Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy, and State Key Laboratory of Biotherapy, Sichuan University, No. 17, Section 3, Renmin Nan Road, Chengdu 610041, China)

Abstract

Due to their architectural intricacy and biological significance, the synthesis of polycyclic diterpenes and their biogenetically related alkaloids have been the subject of considerable interest over the last few decades, with progress including the impressive synthesis of several elusive targets. Despite tremendous efforts, conquering the unique structural types of this large natural product family remains a long-term challenge. The arcutane diterpenes and related alkaloids, bearing a congested tetracyclo[5.3.3.04,9.04,12]tridecane unit, are included in these unsolved enigmas. Here we report a concise approach to the construction of the core structure of these molecules and the first total synthesis of (±)-atropurpuran. Pivotal features of the synthesis include an oxidative dearomatization/intramolecular Diels-Alder cycloaddition cascade, sequential aldol and ketyl-olefin cyclizations to assemble the highly caged framework, and a chemoselective and stereoselective reduction to install the requisite allylic hydroxyl group in the target molecule.

Suggested Citation

  • Jing Gong & Huan Chen & Xiao-Yu Liu & Zhi-Xiu Wang & Wei Nie & Yong Qin, 2016. "Total synthesis of atropurpuran," Nature Communications, Nature, vol. 7(1), pages 1-6, November.
    • Handle: RePEc:nat:natcom:v:7:y:2016:i:1:d:10.1038_ncomms12183
    DOI: 10.1038/ncomms12183
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/ncomms12183
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/ncomms12183?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. Wen Chen & Yonghui Ma & Wenyan He & Yinxia Wu & Yuancheng Huang & Yipeng Zhang & Hongchang Tian & Kai Wei & Xiaodong Yang & Hongbin Zhang, 2022. "Structure units oriented approach towards collective synthesis of sarpagine-ajmaline-koumine type alkaloids," Nature Communications, Nature, vol. 13(1), pages 1-12, 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_ncomms12183. 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.