Back Cover: A Regio- and Diastereoselective Anodic Aryl-Aryl Coupling in the Biomimetic Total Synthesis of (−)-Thebaine (Angew. Chem. Int. Ed. 34/2018)

Eine regio- und diastereoselektive anodische Aryl-Aryl-Kupplung in der biomimetischen Totalsynthese von (−)-Thebain

Rücktitelbild: Eine regio- und diastereoselektive anodische Aryl-Aryl-Kupplung in der biomimetischen Totalsynthese von (−)-Thebain (Angew. Chem. 34/2018)

A Regio- and Diastereoselective Anodic Aryl-Aryl Coupling in the Biomimetic Total Synthesis of (-)-Thebaine.

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.

CCDC 1831234: Experimental Crystal Structure Determination

Related Article: Alexander Lipp, Dorota Ferenc, Christoph Gütz, Mario Geffe, Nina Vierengel, Dieter Schollmeyer, Hans J. Schäfer, Siegfried R. Waldvogel, Till Opatz|2018|Angew.Chem.,Int.Ed.|57|11055|doi:10.1002/anie.201803887

CCDC 1831233: Experimental Crystal Structure Determination

Related Article: Alexander Lipp, Dorota Ferenc, Christoph Gütz, Mario Geffe, Nina Vierengel, Dieter Schollmeyer, Hans J. Schäfer, Siegfried R. Waldvogel, Till Opatz|2018|Angew.Chem.,Int.Ed.|57|11055|doi:10.1002/anie.201803887

CCDC 1831232: Experimental Crystal Structure Determination

Related Article: Alexander Lipp, Dorota Ferenc, Christoph Gütz, Mario Geffe, Nina Vierengel, Dieter Schollmeyer, Hans J. Schäfer, Siegfried R. Waldvogel, Till Opatz|2018|Angew.Chem.,Int.Ed.|57|11055|doi:10.1002/anie.201803887

CCDC 1831236: Experimental Crystal Structure Determination

Related Article: Alexander Lipp, Dorota Ferenc, Christoph Gütz, Mario Geffe, Nina Vierengel, Dieter Schollmeyer, Hans J. Schäfer, Siegfried R. Waldvogel, Till Opatz|2018|Angew.Chem.,Int.Ed.|57|11055|doi:10.1002/anie.201803887

CCDC 1831235: Experimental Crystal Structure Determination

Related Article: Alexander Lipp, Dorota Ferenc, Christoph Gütz, Mario Geffe, Nina Vierengel, Dieter Schollmeyer, Hans J. Schäfer, Siegfried R. Waldvogel, Till Opatz|2018|Angew.Chem.,Int.Ed.|57|11055|doi:10.1002/anie.201803887