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Total Synthesis of (-)-Oxycodone via Anodic Aryl-Aryl Coupling.

Alexander LippMaximilian SeltDorota FerencDieter SchollmeyerSiegfried R WaldvogelJason Sirleaf
Published in: Organic letters (2019)
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.
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