Total synthesis of Epiboxidine:
| Reference: | Armstrong, A.; Bhonoah, Y.; Shanahan, S. E. J. Org. Chem. 2007, 72, 8019 DOI |
| Reactions: | Jones oxidation • Aldehyde → CarboxAcid • Hunsdiecker • C-CO2H → C-Br • Mg-Vinyl+Aldehyde • Mechanism • Amine-5 • Ketone azaenolate+CarboxEster • Isoxazole synthesis • Ni/B-Aryl+Alkyl-Br(2°) • Mechanism • Prins-Pinacol • Bicyclo(221)-aza • EnolEther → Aldehyde-α-amino • Amine-5 • N-Boc → N-H • N-SO2R → N-H • N-SO2R → N-H • N-H → N-Boc • CarboxAcid → CarboxEster • CarboxAcid → CarboxCl • |
| Reagents: | TsNClNa • Vinyl-MgX • CrO3, H2SO4 (Jones) • HgO • Ni(cod)2 • HBr • Boc2O • Acetic acid, trifluoro • SOCl2 • BuLi(n) • HBr • Sulfonyl chloride, methane, NEt3 • SnCl4 • HOMe (react) • |