Combined directed ortho and remote metalation-cross-coupling strategies. General method for benzo[a]carbazoles and the synthesis of an unnamed indolo[2,3-a]carbazole alkaloid.
[reaction: see text] An efficient route to benzo[a]carbazoles via a metalation-cross-coupling sequence has been demonstrated and its application to the synthesis of the antitumor and antiviral alkaloid 6-cyano-5-methoxy-12-methylindolo[2,3-a]carbazole has been achieved.
Cai
Xiongwei
X
Department of Chemistry, Queen's University, Kingston, Ontario K7M 3N6, Canada.
Snieckus
Victor
V
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D007202:Indicators and Reagents; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D046937:Nostoc / Q000737:chemistry*
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D002227:Carbazoles; D007202:Indicators and Reagents; D026121:Indole Alkaloids; D007211:Indoles; C066545:6-cyano-5-methoxy-12-methylindolo(2,3-a)carbazole