Total synthesis of Lycopodine (Stork):
| Reference: | Stork, G.; Kretchmer, R. A.; Schlessinger, R. H. J. Am. Chem. Soc. 1968, 90, 1647-1648. DOI |
| Reactions: | Ketone → EnAmine • Enone+Cu-R • Cu-Me+Enone • ConjAdd Cu-Me • Mg-R → Cu-R • Robinson annulation, ketoester • KetoEster enolate+EnoateEster • Cyclohexenone • 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 • Enone-β-OR → Enone • Enone-β-OR+Al-H • Bicyclo(331) • Alkene isomerization • N-H → N-C(O)OR • Jones oxidation • Alkyl-OH → Ketone • N-C(O)OR → N-H • Lactam-6 • Bicyclo(440)-aza • O-C(O)R → O-H • N-C(O)R → N-CH2R • |
| Reagents: | Acetoacetate • NaOEt • Carbonate, potassium • AlH4-Li+ • Me-MgBr • CuCl2 • Pyrrolidine • Acrylamide • AlH4-Li+ • Li°/NH3 • KOtBu • O=C(OCH2CCl3)Cl (Troc) • O3 • HOMe (react) • SeO2 • H2O2 • NaOMe • Zn° • AlH4-Li+ • CrO3, H2SO4 (Jones) • H3PO4 • Formic acid • |