Total synthesis of Lycopodine (Kraus):
| Reference: | Kraus, G. A.; Hon, Y. S. J. Am. Chem. Soc. 1985, 107, 4341-4342. DOI |
| Reactions: | CompRed-Alkene/Ketone+M-H • Bredt's Rule • ConjAdd Amine • N-H → N-Alkyl • Amine-6 • Mechanism • Bicyclo(440)-aza • Dehydrohalogenation → Enone • Alkyl-OH → Alkyl-Br • Michael Enone • CarboxEster enolate+Enone • ConjAdd Enolate • Aldol-Na → Aldol • Ketone enolate+Ketone • Bicyclo(331) • Decarboxylation β-keto acid • Oppenauer oxidation • Alkyl-OH → Aldehyde • Aldol-K → Enone • Bicyclo(440)-aza • Hydrogenation Enone • Hydroboration → Alkyl-OH • CompRed-Alkene/Ketone+M-H • O-H → O-SO2Ar • |
| Reagents: | NaOMe • Acetoacetate • Hydroxide, sodium • BH3·THF • H2O2, NaOH • Sulfonyl chloride, benzene • PBr3 • DBU • KOtBu • Benzophenone • H2, Pt • |