IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v15y2024i1d10.1038_s41467-024-49748-2.html
   My bibliography  Save this article

Divergent and gram-scale syntheses of (–)-veratramine and (–)-cyclopamine

Author

Listed:
  • Wenlong Hou

    (Sichuan University)

  • Hao Lin

    (Sichuan University)

  • Yanru Wu

    (Sichuan University)

  • Chuang Li

    (Sichuan University)

  • Jiajun Chen

    (Sichuan University)

  • Xiao-Yu Liu

    (Sichuan University)

  • Yong Qin

    (Sichuan University)

Abstract

Veratramine and cyclopamine, two of the most representative members of the isosteroidal alkaloids, are valuable molecules in agricultural and medicinal chemistry. While plant extraction of these compounds suffers from uncertain supply, efficient chemical synthesis approaches are in high demand. Here, we present concise, divergent, and scalable syntheses of veratramine and cyclopamine with 11% and 6.2% overall yield, respectively, from inexpensive dehydro-epi-androsterone. Our synthesis readily provides gram quantities of both target natural products by utilizing a biomimetic rearrangement to form the C-nor-D-homo steroid core and a stereoselective reductive coupling/(bis-)cyclization sequence to establish the (E)/F-ring moiety.

Suggested Citation

  • Wenlong Hou & Hao Lin & Yanru Wu & Chuang Li & Jiajun Chen & Xiao-Yu Liu & Yong Qin, 2024. "Divergent and gram-scale syntheses of (–)-veratramine and (–)-cyclopamine," Nature Communications, Nature, vol. 15(1), pages 1-6, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-49748-2
    DOI: 10.1038/s41467-024-49748-2
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-024-49748-2
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-024-49748-2?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
    ---><---

    References listed on IDEAS

    as
    1. Jussi Taipale & James K. Chen & Michael K. Cooper & Baolin Wang & Randall K. Mann & Ljiljana Milenkovic & Matthew P. Scott & Philip A. Beachy, 2000. "Effects of oncogenic mutations in Smoothened and Patched can be reversed by cyclopamine," Nature, Nature, vol. 406(6799), pages 1005-1009, August.
    Full references (including those not matched with items on IDEAS)

    Most related items

    These are the items that most often cite the same works as this one and are cited by the same works as this one.
    1. Alessandra Ciucci & Ilaria De Stefano & Valerio Gaetano Vellone & Lucia Lisi & Carolina Bottoni & Giovanni Scambia & Gian Franco Zannoni & Daniela Gallo, 2013. "Expression of the Glioma-Associated Oncogene Homolog 1 (Gli1) in Advanced Serous Ovarian Cancer Is Associated with Unfavorable Overall Survival," PLOS ONE, Public Library of Science, vol. 8(3), pages 1-9, March.
    2. Meropi Bagka & Hyeonyi Choi & Margaux Héritier & Hanna Schwaemmle & Quentin T. L. Pasquer & Simon M. G. Braun & Leonardo Scapozza & Yibo Wu & Sascha Hoogendoorn, 2023. "Targeted protein degradation reveals BET bromodomains as the cellular target of Hedgehog pathway inhibitor-1," Nature Communications, Nature, vol. 14(1), pages 1-17, 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:15:y:2024:i:1:d:10.1038_s41467-024-49748-2. 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.

    If CitEc recognized a bibliographic reference but did not link an item in RePEc to it, you can help with 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.