Synthesis of (-)-aphanorphine using aryl radical cyclization.
[structure: see text] The synthesis of (-)-aphanorphine was achieved by using Bu(3)SnH-mediated aryl radical cyclization of 1-benzyloxycarbonyl-2-(2-bromo-4-methoxyphenylmethyl)-2-methoxycarbonyl-4-(phenylthiomethylene)pyrrolidine, leading to exclusive formation of the 6-exo cyclization product.
Tamura
O
O
Faculty of Pharmaceutical Sciences, Kanazawa University, Takara-machi, Kanazawa 920-0934, Japan.
Yanagimachi
T
T
Kobayashi
T
T
Ishibashi
H
H
D001952:Bridged-Ring Compounds / Q000138:chemical synthesis*; D000458:Cyanobacteria / Q000737:chemistry; D003500:Cyclization; D007202:Indicators and Reagents; D011758:Pyrroles / Q000138:chemical synthesis*
D001952:Bridged-Ring Compounds; D007202:Indicators and Reagents; D011758:Pyrroles; C434304:aphanorphine