Functionalization of the 6,14-bridge of the orvinols. 2. Preparation of 18- and 19-hydroxyl-substituted thevinols and their treatment with benzyl bromide

J Org Chem. 2005 Mar 4;70(5):1907-10. doi: 10.1021/jo048388u.

Abstract

The etheno bridge of a thevinone was treated with BH3 and H2O2 to give both the 18- and 19-hydroxyl- substituted thevinols. Selective benzylation of the primary 20-hydroxyl over the 19-hydroxyl was successful; however, benzylation of the 18-hydroxylated product led to a reaction at the more hindered alcohol. Thus, the 6,14-bridge of the Diels-Alder products of thebaine can be hydroxylated, which opens up these positions for further chemical manipulation.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Benzyl Compounds / chemistry*
  • Bridged-Ring Compounds / chemical synthesis*
  • Bridged-Ring Compounds / chemistry
  • Molecular Conformation
  • Morphinans / chemical synthesis*
  • Morphinans / chemistry
  • Narcotics / chemical synthesis*
  • Narcotics / chemistry

Substances

  • Benzyl Compounds
  • Bridged-Ring Compounds
  • Morphinans
  • Narcotics
  • thevinone
  • benzyl bromide