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

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