image

Total synthesis of Strychnine:
Reference: Knight, S. D.; Overman, L. E.; Pairaudeau, G. J. Am. Chem. Soc. 1993, 115, 9293-9294; DOI; Knight, S. D.; Overman, L. E.; Pairaudeau, G. J. Am. Chem. Soc. 1995, 117, 5776- 5788. DOI
Keywords: O-H → O-SiiPr3 • Jones oxidation • Allyl-OH → Enone • EnolTriflate → Sn-Vinyl • Protecting group - Amine • O-SiiPr3 → O-H • O-But → O-H • CarboxEster → Aldehyde • Ether-7 • Lactam-6 • Knoevenagel condensation • Mechanism • ConjAdd M-OR • Ether-7 • Ketone → Imine • Amine-5 • EnoateEster ConjReduct • N-H → N-Allyl • N-H → N-Alkyl • Pd/Sn-Vinyl+Aryl-X+CO • Stille carbonylative coupling • Carbonylation • Pd-enolate allylation • Tsuji-Trost allylation • CompE+-Allyl-X/Allyl-X+Pd-enolate • Enone → EnolTriflate • ConjReduct-Triflation • Enone ConjReduct • Pd-Stannylation • Wittig-methyl • Enone epoxidation, nucleophilic • CompOx-Enone/Alkene+ROOH • Dehydration → Enoate • Claisen acylation, Mander • Ketone enolate+Mander • Mechanism • Mannich • Aza-Claisen • Amine-5 • Ketone → Alkyl-OH • CompRed-Ketone/CarboxEster+M-H • O-H → O-C(O)OR • EnoateEster → Allyl-OH • O-H → O-SO2R • Finkelstein reaction • Allyl-X → Allyl-Cl • Epoxide+NR2 • Amine-6 • N-C(O)R → N-H •
Reagents: O=C(OR)Cl • NaH • Pd2(dba)3 • BH3CN-Na+ • TiCl4 • Carbodiimide • CuCl • AlHiBu2 • SiiPr3-Cl • CrO3, H2SO4 (Jones) • BH(Et)3-Li+ • Tf2NPh • SnMe3-SnMe3 • Pd(PPh3)4 • Pd2(dba)3 • AsPh3 • CO • Hydroperoxide, tbutyl • Triton B • PPh3=CH2 • Fluoride, R4N+ • Sulfonyl chloride, methane • NEtiPr2 • Chloride, lithium • Acetamide, trifluoro • NaH • Epoxide • NaH • Hydroxide, potassium • LiNiPr2 • O=C(OR)CN • HCl, MeOH • Zn° • H2SO4 • NaOMe • AlHiBu2 • Malonic acid • Acetic anhydride • DMF (solvent) • Formaldehyde • Sulfide, sodium •

Syntheses Home