The protoberberine→spirobenzylisoquinoline→dibenzocyclopent[b]azepine rearrangement
Abstract
Base-catalysed rearrangement of the monophenolic dihydroprotoberberine salts (5) and (7) leads to the spirobenzylisoquinolines (6) and (8) respectively, while rearrangement of the salt (9) furnishes the dibenzocyclopent[b]azepine (14).