Concise total synthesis of the aporphine alkaloid 7,7-bisdehydro-O-methylisopiline by an InCl3 mediated cycloisomerization reaction

A novel InCl3 mediated cycloisomerization reaction leading to 10-halophenanthrene derivatives constitutes the key step of the first total syntheses of O-methyldehydroisopiline 10 and 7,7ʹ-bisdehydro-O-methylisopiline 11, two prototype members of the aporphine family of alkaloids.