Synthesis of (−)-Aphanorphine Using
Aryl Radical Cyclization

Tamura, Osamu; Yanagimachi, Takehiko; Kobayashi, Tetsuya; Ishibashi, Hiroyuki

doi:10.1021/ol015818j.s001

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Synthesis of (−)-Aphanorphine Using Aryl Radical Cyclization

journal contribution

posted on 2001-07-07, 00:00 authored by Osamu Tamura, Takehiko Yanagimachi, Tetsuya Kobayashi, Hiroyuki Ishibashi

The synthesis of (−)-aphanorphine was achieved by using Bu₃SnH-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.