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

  title={Total Synthesis of (-)-Oxycodone via Anodic Aryl-Aryl Coupling.},
  author={A. Lipp and Maximilian Selt and D. Ferenc and D. Schollmeyer and S. Waldvogel and T. Opatz},
  journal={Organic letters},
  volume={21 6},
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… Expand
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