Improving Alkyne Metathesis for Natural Products

  • Author: Pamela Alsabeh
  • Published Date: 05 June 2016
  • Source / Publisher: Chemistry – A European Journal/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Improving Alkyne Metathesis for Natural Products

Related Societies

Using molybdenum-alkylidene-siloxy complexes as catalysts for alkyne metathesis significantly improves the reaction with respect to catalytic activity and functional group tolerance. However, challenges still remain for known catalyst systems in terms of ease of synthesis, scale-up, and application to problematic substrates, e.g., those with protic sites.

Alois Fürstner and colleagues, Max Planck Institute (MPI) for Coal Research, Mülheim an der Ruhr, Germany, have addressed these challenges by combining a tris(amido)molybdenum alkylidene complex and easily synthesized trisilanol ligands. This new two-component catalyst provides excellent functional group tolerance in alkyne metathesis, including alkynes bearing primary, secondary, or phenolic OH groups. It also works well for (bis)propargylic alcohol derivatives.

The researchers used the method to synthesize natural products such as manshurolide, a sesquiterpene lactone found in Manchurian pipevine, and ivorenolide A, a macrolide found in African mahogany. They also demonstrated the first alkyne metathesis of a substrate with three different triple bonds, two of which underwent catalysis, whereas the third remained untouched. These results are a progress for alkyne chemistry and could inform further catalyst design.


Article Views: 3028

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

Bookmark and Share

If you would like to reuse any content, in print or online, from, please contact us first for permission. more

CONNECT: on Facebook on Twitter on YouTube on LinkedIn Sign up for our free newsletter

Magazine of Chemistry Europe (16 European Chemical Societies)published by Wiley-VCH