Total synthesis of Strychnine (Woodward):
| Reference: | Woodward, R. B.; Cava, M. P.; Ollis, W. D.; Hunger, A.; Daeniker, H. U.; Schenker, K. J. Am. Chem. Soc. 1954, 76, 4749-4751; DOI Woodward, R. B.; Cava, M. P.; Ollis, W. D.; Hunger, A.; Daeniker, H. U.; Schenker, K. Tetrahedron 1963, 19, 247-288. DOI |
| Reactions: | N-H → N-SO2R • Amine-5 • N-SO2R → N-H • N-H → N-C(O)R • CarboxAcid → CarboxEster • O-H → O-SO2Ar • EnoateEster Hydrogenation • CarboxEster → CarboxAcid • Mechanism • Fischer Indole • Indole synthesis • Dieckmann • CarboxEster enolate+CarboxEster • Cyclohexanone • Mechanism • Ether-7 • Mannich • Amine-5 • Spiro(44) • CarboxEster epimerization • Hydrogenolysis C-S • Alkyl-SR → Alkyl-H • N-C(O)R → N-CH2R • Mechanism • CarboxAmide enolate+EnoateEster • Retro-Michael • Mechanism • Allyl-OR isomerization • ConjAdd M-OR • Enol → EneSulfide • Nitrile → Amine • Mannich • Claisen acylation, acyl-X • CarboxEster enolate+Acyl-X • Ketone → Ketone-1,2-di • Ketone-1,2-di • Alkyl-NR2 → Alkyl-CN • Amine → Ammonium • Lactam-6 • Na-Alkynyl+Ketone • CompE+-Ketone/CarboxAmide+M-R • Alkyne → Ene-cis (Lindlar) • Aldehyde → Imine • Imine → Amine • N-H → N-C(O)R • Ozonolysis Ph • |
| Reagents: | Hydrazine, phenyl • Polyphosphoric acid • Formaldehyde • NHMe2 • MeI • Cyanide, sodium • AlH4-Li+ • Glyoxalate • TsCl, Py • BH4-Na+ • Acetic anhydride, Py • O3 • HCl, MeOH • HI • Acetic anhydride • Diazomethane • NaOMe • TsCl, Py • Thiolate, benzyl • RaNi • H2, Pd • Hydroxide, potassium • Acetic anhydride, Py • HCl, AcOH • SeO2 • Alkynyl-Na • H2, Pd • H2SO4 • AlH4-Li+ • HBr • Hydroxide, potassium • P°(red) • CH2=NMe2+I- • |