Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 34, Pages 11055-11059Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201803887
Keywords
alkaloids; biomimetic synthesis; electrochemistry; morphine; thebaine
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Funding
- Advanced Lab of Electrochemistry and Electrosynthesis (ELYSION - Carl-Zeiss-Foundation)
- Rhineland Palatinate Natural Products Research Center
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The biosynthesis of thebaine is based on the regioselective, intramolecular, oxidative coupling of (R)-reticuline. For decades, chemists have sought to mimic this coupling by using stoichiometric oxidants. However, all approaches to date have suffered from low yields or the formation of undesired regioisomers. Electrochemistry would represent a sustainable alternative in this respect but all attempts to accomplish an electrochemical synthesis of thebaine have failed so far. Herein, a regio- and diastereoselective anodic coupling of 3,4,5-trioxygenated laudanosine derivatives is presented, which finally enables electrochemical access to (-)-thebaine.
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