Electrooxidative Cyclization of 1-Benzyltetrahydroisoquinolines. A Novel Nonphenol Coupling Reaction

L. L. Miller, F. R. Stermitz, J R Falck

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59 Scopus citations

Abstract

(±)-Laudanosine was oxidized at platinum in a three-compartment cell at 1.1 V in acetonitrile at 0° in the presence of Na2CO3. Either lithium perchlorate or tetramethylammonium tetrafluoroborate was the background electrolyte. O-Methylflavinantine was isolated from the anolyte in 52 % yield. Similar oxidation of (±)-O-benzylcodamine, (±)-O-benzylpseudocodamine, (±)-O-benzyllaudanine, and (±)-O-benzylpseudolaudanine yielded O-methylflavinantine, O-benzylflavinantine, O-benzylisoflavinantine, and 2,3-dimethoxy-6-benzyloxymorphinandienone, respectively. Oxidation of (±)-laudanosine in the presence of equal molar bis(acetonitrile)- palladium(II) chloride enhanced the O-methylflavinantine yield to 63 %.

Original languageEnglish (US)
Pages (from-to)2651-2656
Number of pages6
JournalJournal of the American Chemical Society
Volume95
Issue number8
DOIs
StatePublished - Apr 1 1973

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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