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Total synthesis of Loline:
Reference: Tufariello, J. J.; Meckler, H.; Winzenberg, K. J. Org. Chem. 1986, 51, 3556. DOI
Keywords: Ketone → Ketal(Me) • Hydroxylamine → Nitrone • O-H → O-SO2R • CarboxEster → Alkyl-OH • O-H → O-C(O)R • Ketal → Ketone • Jones oxidation • Alkyl-OH → CarboxAcid • CompOx-Alcohol/Amine+CrO3 • Fischer esterification • CarboxAcid → CarboxEster • CarboxEster → CarboxHydrazide • Curtius • C-CO2H → C-N • Hydrogenolysis N-O • Hydrogenation Ketone • N-H → N-Alkyl • Amine-5 • Alkyl-OH → Alkyl-Cl • Williamson etherification • Ether-5 • N-C(O)OR → N-Me • Cope elimination • Nitrone Cycloaddition • CarboxEster epimerization •
Reagents: Orthoformate • HCl, MeOH • HgO • Sulfonyl chloride, methane, NEt3 • H2, Pd • AlH4-Li+ • Acetic anhydride • Acetic acid, trifluoro • Bicarbonate, sodium • H2, Pt • SOCl2 • DMF (solvent) • NaOMe • CrO3, H2SO4 (Jones) • H2SO4 • Hydrazine • Amyl nitrite • AlH4-Li+ • Crotonate • NaOMe •

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