Total synthesis of Sceletium Alkaloid A-4:
| Reference: | Stevens, R. V.; Lesko, P. M.; Lapalme, R. J. Org. Chem. 1975, 40, 3495. DOI |
| Reactions: | Nitrile anion+Alkyl-X • Cyclopropane • Alkyl-X+Nitrile anion (intram) • Robinson annulation, enamine • Aldehyde enamine+Enone • Enone+EnAmine • ConjAdd EnAmine • Bicyclo(430)-aza • Nitrile → Aldehyde • Aldehyde enamine+Enone • Enone+EnAmine • Pyridine synthesis • 1,3-Sigmatropic • Amine-5 • CarboxEster → Aldehyde • Ketone → Ketal(Me) • Aldehyde → Imine • |
| Reagents: | Ethylene dichloride • LiNiPr2 • AlHiBu2 • NH2Me • Methyl vinyl ketone • Ethyl vinyl ketone • Orthoformate • AlHiBu2 • NH2OH • Iodide, ammonium • HMPA (solvent) • |