image

Total synthesis of Strychnine:
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
Keywords: N-H → N-SO2R • Amine-5 • Imine → Amine • N-H → N-Bn • N-SO2R → N-H • N-H → N-C(O)R • O-H → O-SO2R • Na-Alkynyl+Ketone • Mechanism • Fischer Indole • Indole synthesis • Dieckmann • CarboxEster enolate+CarboxEster • Mechanism • Ether-7 • Mannich • Amine-5 • CarboxEster epimerization • Hydrogenolysis C-S • CompE+-Ketone/CarboxAmide+Na-Alkynyl • CarboxAmide → Amine • Mechanism • Mechanism • Allyl-OH isomerization • ConjAdd M-OR • Enol → EneSulfide • Nitrile → Amine • Aldehyde → Imine • Mannich • Claisen acylation, acyl-X • CarboxEster enolate+CarboxAnhydride • Ozonolysis Ph • Ketone → Ketone-1,2-di • Ketone-1,2-di •
Reagents: Hydrazine, phenyl • Polyphosphoric acid • Formaldehyde • CH2=NMe2+I- • MeI • Cyanide, sodium • AlH4-Li+ • 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 • HCl • Acetic acid • SeO2 • Alkynyl-Na • H2, Pd • H2SO4 • AlH4-Li+ • HBr • Hydroxide, potassium • P°(red) •

Syntheses Home