Total synthesis of Loline:
| Reference: | Tufariello, J. J.; Meckler, H.; Winzenberg, K. J. Org. Chem. 1986, 51, 3556. DOI |
| Reactions: | Curtius • C-CO2H → C-N • N-OR → N-H • Hydrogenation Ketone • N-H → N-Alkyl • Amine-5 • Bicyclo(330)-aza • Alkyl-OH → Alkyl-Cl • Williamson etherification • Ether-5 • O-C(O)R → O-H • Bicyclo(221)-aza • N-C(O)OR → N-CH3 • Cope elimination • Nitrone Cycloaddition • CarboxEster epimerization • O-H → O-SO2Me • CarboxEster → CarboxHydrazide • Ketone → Ketal(Me) • Hydroxylamine → Nitrone • Jones oxidation • Alkyl-OH → CarboxAcid • CompOx-Alkyl-OH/Amine+CrO3 • CarboxEster → Alkyl-OH • O-H → O-C(O)R • Fischer esterification • CarboxAcid → CarboxEster • |
| 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 • HOMe (react) • HOEt (react)} • |