6533b85efe1ef96bd12c086f
RESEARCH PRODUCT
A Regio- and Diastereoselective Anodic Aryl-Aryl Coupling in the Biomimetic Total Synthesis of (-)-Thebaine.
Dorota FerencHans J. SchäferSiegfried R. WaldvogelAlexander LippMario GeffeNina VierengelTill OpatzChristoph GützDieter Schollmeyersubject
Thebaine010405 organic chemistryArylTotal synthesisRegioselectivityGeneral Chemistry010402 general chemistry01 natural sciencesCombinatorial chemistryCatalysis0104 chemical scienceschemistry.chemical_compoundchemistryBiomimetic synthesisIntramolecular forceStructural isomermedicineOxidative coupling of methanemedicine.drugdescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2018-04-01 | Angewandte Chemie (International ed. in English) |