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A Regio‐ and Diastereoselective Anodic Aryl–Aryl Coupling in the Biomimetic Total Synthesis of (−)‐Thebaine
Author(s) -
Lipp Alexander,
Ferenc Dorota,
Gütz Christoph,
Geffe Mario,
Vierengel Nina,
Schollmeyer Dieter,
Schäfer Hans J.,
Waldvogel Siegfried R.,
Opatz Till
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201803887
Subject(s) - thebaine , chemistry , regioselectivity , aryl , electrochemistry , combinatorial chemistry , oxidative coupling of methane , coupling reaction , structural isomer , sesamol , organic chemistry , catalysis , electrode , morphine , medicine , alkyl , codeine , pharmacology , antioxidant
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.