Acid catalyzed rearrangement and acyl migration studies on 9-dihydro-13-acetylbaccatin-III, a major taxane from Taxus canadensis

Abstract A detailed investigation of the rearrangement of the major taxane from Taxus canadensis enables to suggest the sequence of the reactions involved: 9-dihydro- 13-acetylbaccatin III → abeo -taxanes with intact oxetane and acyl migration → abeo -taxanes with intact oxetane and deacylation → abeo -taxanes with opening of the oxetane and various acyl migrations including two unusual benzoyl shifts.