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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 • Decarboxylation • N-Bn → N-H • Diels-Alder-inverse, Enamine • Amine-5 • Amine-5 • Aldehyde → Acetal(Me) • CarboxEster → Alkyl-OH • Acetal → Aldehyde • Mechanism • Alkyl-OH → Alkyl-Br • Finkelstein reaction • 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 •
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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