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Total synthesis of Vincadifformine:
Reference: Kuehne, M. E.; Roland, D. M.; Hafter, R. J. Org. Chem. 1978, 43, 3705. DOI
Keywords: Mechanism • N-Bn → N-H • Diels-Alder-inverse, EnAmine • Amine-5 • Amine-5 • Aldehyde → Acetal(Me) • O-H → O-SO2R • Alkyl-X → Alkyl-Br • Finkelstein reaction • Mechanism • Alkyl-OH → Alkyl-Br • Aldehyde enamine+EnoateEster • ConjAdd EnAmine • Hofmann elim → Enoate • Aldehyde → EnAmine • Aldehyde enamine+Alkyl-X • Amine-6 • Alkyl-X+EnAmine • EnAmine → Imine-α-Cl • Amine-7 • Decarboxylation malonic • CarboxEster → Alkyl-OH • Acetal → Aldehyde • CarboxEster enolate+Imine •
Reagents: Carbonate, potassium • DMF (solvent) • Hypochlorite, tbutyl • Malonate • Thalium malonate • Acetic acid, trifluoro • H2, Pd • AlH4-Li+ • Sulfonyl chloride, methane, NEt3 • Bromide, lithium • Acrylate • DMF (solvent) • Acetic acid •

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