Total synthesis of Alantolactone:
| Reference: | Marshall, J. A.; Cohen, N. J. Am. Chem. Soc. 1965, 87, 2773-2774. DOI |
| Reactions: | O-C(O)R → O-H • Alkyl-OH → Ketone • Enone enolate+Alkyl-X • Alkyl-X+Enolate • Enone+Li-R • Li-Me+Ketone • Cationic cyclization • Cyclohexane • Bicyclo(440) • Ketone enamine+Alkyl-X • Bromoacetate+EnAmine • Claisen acylation, carbonate • CarboxEster enolate+Carbonate • MalonicEster → Allyl-OH • Allyl-OH → EnoateEster • CompOx-Allyl-OH/Alkyl-OH+MnO2 • Lactone-5 • Singlet oxygen+Alkene • Allylic oxidation → Allyl-OH • CarboxEster → CarboxAcid • CarboxAcid → CarboxEster • Ketone → Alkyl-OH • CompRed-Ketone/CarboxEster+M-H • Lactone-5 • Hydrogenation Alkene • Dehydration → Ene • Ketone → Enamine • O-OH → O-H • Decarboxylation β-keto acid • CarboxEster → CarboxAcid • |
| Reagents: | NaH • Me-Li • Formic acid • Hydroxide, sodium • CrO3, H2SO4 (Jones) • Pyrrolidine • Bromoacetate • Hydroxide, potassium • Diazomethane • BH4-K+ • O2 (singlet) • H2, Pd • SOCl2 • NaH • O=C(OR)2 • AlH4-Li+ • MnO2 • Hagemann's ester • Hydroxide, sodium • |