Electrooxidative synthesis of morphinandienones from 1-benzyltetrahydroisoquinolines

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

Research output: Contribution to journalArticle

34 Scopus citations

Abstract

The electrochemical oxidation of several 1-benzyl tetrahydroisoquinolines has been performed at a platinum anode in acetonitrile. Using potentiostatic conditions and a three compartment cell, the following cyclizations were accomplished on a several hundred milligram scale in the yields indicated: 6′-bromolaudanosine to O-methylflavinantine (16%), 5′-methoxylaudanosine to O-methyl-C-norandrocymbine (38%), 8-methoxylaudanosine to protostephanone (35%), norlaudanosine to N-nor-O-methylflavinantine (22%).

Original languageEnglish (US)
Pages (from-to)931-934
Number of pages4
JournalTetrahedron
Volume30
Issue number8
DOIs
StatePublished - 1974

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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