title: Functionalization of the 6,14-bridge of the orvinols. 2. Preparation of 18- and 19-hydroxyl-substituted thevinols and their treatment with benzyl bromide.
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.
authors.affiliation: Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy, 20 Penn Street, Room 637, Baltimore, Maryland 21201, USA.
authors.forename: Huifang
authors.initials: H
authors.lastname: Wu
authors.forename: Denzil
authors.initials: D
authors.lastname: Bernard
authors.forename: Weibin
authors.initials: W
authors.lastname: Chen
authors.forename: Gary D
authors.initials: GD
authors.lastname: Strahan
authors.forename: Jeffrey R
authors.initials: JR
authors.lastname: Deschamps
authors.forename: Damon A
authors.initials: DA
authors.lastname: Parrish
authors.forename: John W
authors.initials: JW
authors.lastname: Lewis
authors.forename: Alexander D
authors.initials: AD
authors.lastname: MacKerell
authors.forename: Andrew
authors.initials: A
authors.lastname: Coop
mesh_terms: D001593:Benzyl Compounds / Q000737:chemistry*; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D009019:Morphinans / Q000138:chemical synthesis* / Q000737:chemistry; D009294:Narcotics / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001593:Benzyl Compounds; D001952:Bridged-Ring Compounds; D009019:Morphinans; D009294:Narcotics; C105913:thevinone; C038682:benzyl bromide