IDEAS home Printed from https://ideas.repec.org/a/nat/nature/v453y2008i7199d10.1038_nature07046.html
   My bibliography  Save this article

The total synthesis of (-)-cyanthiwigin F by means of double catalytic enantioselective alkylation

Author

Listed:
  • John A. Enquist Jr

    (The Arnold and Mabel Beckman Laboratories of Chemical Synthesis, California Institute of Technology, 1200 East California Boulevard, MC164-30, Pasadena, California 91125, USA)

  • Brian M. Stoltz

    (The Arnold and Mabel Beckman Laboratories of Chemical Synthesis, California Institute of Technology, 1200 East California Boulevard, MC164-30, Pasadena, California 91125, USA)

Abstract

Complex synthesis: Doubling up The utility of a 'double catalytic enantioselective reaction' is demonstrated by the rapid protecting group-free synthesis of the diterpenoid (−)-cyanthiwigin F, a natural marine product originally isolated from the sea sponge Myrmekioderma styx. Double catalytic enantioselective reactions have the potential to construct stereochemically complex molecules in a single operation by creating several stereocentres at remote points within the same molecular scaffold. The key step in the nine-step synthesis of cyanthiwigin F is the conversion of a complicated mixture of racemic and meso diastereomers into a synthetically useful intermediate with exceptional enantiomeric excess.

Suggested Citation

  • John A. Enquist Jr & Brian M. Stoltz, 2008. "The total synthesis of (-)-cyanthiwigin F by means of double catalytic enantioselective alkylation," Nature, Nature, vol. 453(7199), pages 1228-1231, June.
    • Handle: RePEc:nat:nature:v:453:y:2008:i:7199:d:10.1038_nature07046
    DOI: 10.1038/nature07046
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/nature07046
    File Function: Abstract
    Download Restriction: Access to the full text of the articles in this series is restricted.
    File URL: https://libkey.io/10.1038/nature07046?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
    ---><---

    As the access to this document is restricted, you may want to search for a different version of it.

    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:nature:v:453:y:2008:i:7199:d:10.1038_nature07046. 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.