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RESEARCH PRODUCT
Total Synthesis of (-)-Oxycodone via Anodic Aryl-Aryl Coupling.
Maximilian SeltSiegfried R. WaldvogelDorota FerencAlexander LippDieter SchollmeyerTill Opatzsubject
010405 organic chemistrySinglet oxygenArylOrganic ChemistryTotal synthesis010402 general chemistryElectrochemistry01 natural sciencesBiochemistryCombinatorial chemistryCycloaddition0104 chemical sciencesHydroxylationchemistry.chemical_compoundchemistryNucleophilic substitutionPhysical and Theoretical ChemistryConjugatedescription
A fully regio- and diastereoselective electrochemical 4a–2′-coupling of a 3′,4′,5′-trioxygenated laudanosine derivative enables the synthesis of the corresponding morphinandienone. This key intermediate is further transformed into (−)-oxycodone through conjugate nucleophilic substitution for E-ring closure and [4 + 2] cycloaddition with photogenerated singlet oxygen to accomplish diastereoselective hydroxylation at C-14. The anodic transformation provides high yields and can be performed under constant current conditions both in a simple undivided cell or in continuous flow.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2019-02-19 | Organic letters |