Electrooxidative synthesis of morphinandienones from 1-benzyltetrahydroisoquinolines

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

Research output: Contribution to journalArticle

34 Citations (Scopus)

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

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Tetrahydroisoquinolines
Electrochemical oxidation
Cyclization
Platinum
Anodes
Electrodes
acetonitrile
morphinandienone

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Electrooxidative synthesis of morphinandienones from 1-benzyltetrahydroisoquinolines. / Falck, J R; Miller, L. L.; Stermitz, F. R.

In: Tetrahedron, Vol. 30, No. 8, 1974, p. 931-934.

Research output: Contribution to journalArticle

Falck, J R ; Miller, L. L. ; Stermitz, F. R. / Electrooxidative synthesis of morphinandienones from 1-benzyltetrahydroisoquinolines. In: Tetrahedron. 1974 ; Vol. 30, No. 8. pp. 931-934.
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