Total synthesis of Luciduline (Oppolzer):
| Reference: | Oppolzer, W.; Petrzilka, M. J. Am. Chem. Soc, 1976, 98, 6722. DOI |
| Reactions: | Diels-Alder, Enone • Bicyclo(440) • Reductive amination, B-H • N-OR → N-H • Nitrone Cycloaddition • Amine-6 • Aldehyde → Nitrone • Nitrone synthesis • Ketone → Oxime • Amine → Ammonium • Jones oxidation • Alkyl-OH → Ketone • CompOx-Alkyl-OH/Amine+CrO3 • |
| Reagents: | SnCl4 • Acetonitrile (solvent) • NH2OH • Acetate, sodium • BH3CN-Na+ • Formaldehyde • AlH4-Li+ • CrO3, H2SO4 (Jones) • Butadiene • MeOSO2F • |