The isoindolobenzazepine alkaloids

Three Chilean barberries, $\text{Berberis}$$\text{actinacantha}$ Mart. ex Schult., $\text{B}$. $\text{darwinii}$ Hook and [ulbar|B. $\text{valdiviana}$Phil. (Berberidaceae), have yielded several new isoindolobenzazepine and protoberberine alkaloids. Novel isoindolobenzazepines are (±)-13-deoxychilenine ($\text{a}$), pictonamine ($\text{10}$), chileninone ($\text{12}$), (±)-chileniimi ($\text{18}$) and (±)-palmanine ($\text{19}$). Highly oxidized protoberberines of particular interest include (±)-O-methylprechilenine ($\text{6}$) and (±)-prepseudopalmanine ($\text{21}$), together with 13-methoxy-8-oxyberberine ($\text{8}$). Isoindolobenzazepine alkaloids arise biogenetically from the rearrangement of highly oxidized protoberberines.