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Total synthesis of Crinine:
Reference: Whitlock, H. W.; Smith, G. L. J. Am. Chem. Soc., 1967, 89, 3600 DOI
Keywords: Enone → Allyl-OH • Pictet-Spengler • Li-Nitrile+CarboxEster • CarboxEster+Li-Nitrile • Nitrile → CarboxEster • Decarboxylation • Claisen acylation, ester • Ketone enolate+CarboxEster • Aziridine • ConjAdd Amine • Imine → Amine • Ketone → Ketone-α-Halo • Dehydrohalogenation → Enone • Allyl-OH isomerization • 1,3-Sigmatropic • Amine-5 •
Reagents: NaOEt • HCl, MeOH • Acetic acid • NaOMe • Aziridine • H2, Pt • Bromine • Acetic acid • Chloride, lithium • DMF (solvent) • AlH4-Li+ • BuLi(n) • TsCl, Py • Iodide, sodium •

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