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