175657-03-1Relevant academic research and scientific papers
Synthesis of 7-arylmorphinans. Probing the 'address' requirements for selectivity at opioid δ receptors
Gao, Peng,Larson, Dennis L.,Portoghese, Philip S.
, p. 3091 - 3098 (2007/10/03)
Through arylation of 6-keto opiates with diaryliodonium iodide, a series of 7-aryl opiates (38) have been prepared in an effort to investigate the effect of conformational mobility of the δ 'address' moiety on opioid agonist and antagonist potencies. Eval
Boron tribromide-catalyzed rearrangement of 7,7-diphenylhydromorphone to 6,7-diphenylmorphine: A novel conversion of ketones to allylic alcohols
Gao, Peng,Portoghese, Philip S.
, p. 2466 - 2469 (2007/10/03)
A novel boron tribromide-catalyzed rearrangement of ketones to allylic alcohols was discovered in the 7-phenylmorphinan-6-one system. The reaction involved the stereospecific migration of an axial 7β-phenyl (or a hydrogen) to the C-6 carbonyl carbon, followed by the elimination of the H-8 proton leading to the generation of allylic alcohols. A possible mechanistic pathway for this rearrangement is discussed.
