Studies on Morphine Alkaloids. II. Indolinocodeine. I. A New Skeletal Rearrangement of 14-Bromocodeine

Abstract

Neopine (III), isoneopine (XXII) and indolinocodeine (XVII) were isolated from the sodium borohydride reduction mixture of 14-bromocodeinone (I) or 14-bromocodeine (II). The structures of new compounds, XVII and XXII, were elucidated. Hydroindole structure is comprised in XVII instead of hydroisoquinoline skeleton in codeine. The reaction mechanisms for production of the above three compounds were also discussed.