Total synthesis of Matrine:
| Reference: | Mandell, L.; Gresham, J. T.; Freeman, W. J. J. Am. Chem. Soc. 1965, 87, 5234–5236. DOI |
| Reactions: | KetoEster → EnAmine • Hydrogenation EnoateEster • Dieckmann • CarboxEster enolate+CarboxEster • Amine-6 • Bicyclo(440)-aza • Decarboxylation β-keto acid • Ketone enamine+EneNitrile • EneNitrile+Enamine • ConjAdd EnAmine • Reductive amination, H2 • Nitrile → Amine • Mechanism • Amine-6 • Bicyclo(440) • Ketone → EnAmine • CarboxEster → Carboxamide • Lactam-6 • |
| Reagents: | Acetoacetate • H2, Pt • NaH • Acetic acid • Pyrrolidine • Acrylonitrile • H2, Pd • Acetic acid • |