image

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

Syntheses Home