Total synthesis of Aspidospermine (Stork):
| Reference: | Stork, G.; Dolfini, J. E. J. Am. Chem. Soc. 1963, 85, 2872-2873. DOI |
| Reactions: | Aldehyde → EnAmine • Aldehyde → EnAmine • ConjAdd EnAmine • ConjAdd EnAmine • Robinson annulation, enamine • Cyclohexenone • Enone → Ketal • CarboxEster → Carboxamide • Ketal → Enone • N-C(O)R → N-CH2R • ConjAdd Amine • Amine-6 • Bicyclo(440)-aza • N-H → N-C(O)R • Ketone enolate+Alkyl-X (intram) • Alkyl-X+Enolate (intram) • Lactam-5 • Bicyclo(430) • Fischer Indole • Indole synthesis • Ketone → Hydrazone • Imine → Amine • Ketone → Ketal • N-C(O)R → N-CH2R • Ketal → Ketone • N-H → N-C(O)R • |
| Reagents: | Pyrrolidine • Acrylate • Acetic acid • Methyl vinyl ketone • Glycol • AlH4-Li+ • Acryloyl-Cl • KOtBu • Glycol • AlH4-Li+ • Hydrazine, phenyl • Acetic acid • AlH4-Li+ • Acetic anhydride • |