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Total synthesis of Sceletium Alkaloid A-4:
Reference: Stevens, R. V.; Lesko, P. M.; Lapalme, R. J. Org. Chem. 1975, 40, 3495. DOI
Keywords: Li-Nitrile+Alkyl-X • Cyclopropane • Alkyl-X+Enolate • Robinson annulation, enamine • Aldehyde enamine+Enone • Enone+EnAmine • ConjAdd EnAmine • 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, HMPA • AlHiBu2 • NH2Me • HCl • Methyl vinyl ketone • Ethyl vinyl ketone • Orthoformate • AlHiBu2 • HCl • NH2OH • HCl • Iodide, ammonium • HMPA (solvent) •

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