image

Total synthesis of Lycopodine:
Reference: Stork, G.; Kretchmer, R. A.; Schlessinger, R. H. J. Am. Chem. Soc. 1968, 90, 1647-1648. DOI
Keywords: Enone-β-OR+Al-H • Enone-β-OR → Enone • CarboxAmide → Amine • Alkene isomerization • N-H → N-C(O)OR • Lactam-6 • N-C(O)OR → N-H • Jones oxidation • Alkyl-OH → Ketone • Enone-β-X+Cu-R • Cu-Me+Enone-β-X • ConjAdd Cu-R • Robinson annulation, ketoester • Ketoester enolate+EnoateEster • Ketone enamine+EnoateAmide • ConjAdd Enamine • Birch reduction • Baeyer-Villiger • Ketone → EnolEther • CarboxAmide → Amine • Ozonolysis • CompOx-Alkene/Alkene+O3 • Friedel-Crafts Alkylation • Mechanism • Lactam-6 • Mechanism •
Reagents: Acetoacetate • NaOEt • Carbonate, potassium • AlH4-Li+ • MeMgBr • CuCl2 • Acrylamide • AlH4-Li+ • Li°/NH3 • KOtBu • O3 • SeO2 • H2O2 • NaOMe • Zn° • AlH4-Li+ • CrO3, H2SO4 (Jones) • H3PO4 • Formic acid •

Syntheses Home