Total Synthesis of a Natural Herbicide

  • Author: Chemistry – A European Journal
  • Published Date: 04 July 2019
  • Source / Publisher: Chemistry – A European Journal/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Total Synthesis of a Natural Herbicide

Related Societies

The oxepine ring and its hydrogenated versions are present in a wide variety of natural products. The total synthesis of these products has mainly been achieved using C–C-bond-forming ring-closing metathesis or C–O-bond-forming nucleophilic substitutions. Sigmatropic rearrangements of 2-vinylcyclopropanecarbonyl substrates could be an alternative to these reactions. However, this approach has been hampered by the metastability of the 2,5-dihydrooxepine intermediates, which strongly depends on their substitution pattern.

Wei Zhang, Bastien Nay, Gilles Frison (Ecole Polytechnique de Paris, France), and colleagues have developed a one-pot method to synthesize bicyclic 2,5-dihydrooxepines. The team used a tandem vinylcyclopropanation/retro-Claisen rearrangement (pictured below), starting from 1,3-cyclohexadione derivatives. These reactions were carried out under strict temperature control to minimize the formation of competing dihydrofuran products.

The one-pot approach was successfully used for a short total synthesis of radulanin A (pictured above), a natural 2,5-dihydrobenzoxepine isolated from liverwort. The team used thale cress seedlings to evaluate the herbicidal potential of this natural product. Its activity was comparable to that of glyphosate, which is used as a reference herbicide. This discovery has been patented and the team hopes that it leads to a new class of natural weed-killing compounds.



Article Views: 1709

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