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 7,7'-bisdehydro-O-methylisopiline 11, two prototype members of the aporphine family of alkaloids.
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001060:Aporphines / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007204:Indium / Q000737:chemistry*; D007536:Isomerism
C442599:7,7'-bis(dehydro-O-methylisopiline); D000470:Alkaloids; D001060:Aporphines; D007204:Indium; C081279:aporphine; C020758:indium trichloride