Total synthesis of Anatoxin A:
| Reference: | Brenneman, G. B.; Martin, S. F. Org. Lett. 2004, 6, 1329. DOI |
| Reactions: | CarboxEster → Aldehyde • N-Cbz → N-H • Li-Alkynyl+Alkyl-X • Na/H → Na-Alkynyl • CarboxAmide → Ketone • Mg-Alkyl+CarboxAmide • CompE+-Carboximide/CarboxEster+M-R • CarboxEster → Aldehyde • CompRed-CarboxEster/Carbamate+M-H • Lemieux-Johnson oxidation • Alkene cleavage • CompOx-Alkene/Alkene+OsO4 • Seyferth-Gilbert homologation • Aldehyde → Alkyne • Reductive amination, Si-H • Amine-5 • CompRed-Ketone/CarboxEster+M-H • Enyne metathesis • Amine-7 • Bicyclo(421)-aza • |
| Reagents: | Alkyl-MgX • BF3·OEt2 • HSiPh3 • Diazophosphonate • AlHiBu2 • NaN(SiMe3)2 • MeOTf • OsO4, NaIO4 • SiMe3-I • Imidazole • Grubbs II • |