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Total synthesis of Alantolactone:
Reference: Marshall, J. A.; Cohen, N. J. Am. Chem. Soc. 1965, 87, 2773-2774. DOI
Keywords: O-C(O)R → O-H • Alkyl-OH → Ketone • CarboxEster → CarboxAcid • CarboxEster → CarboxAcid • Ketone → Alkyl-OH • Dehydration → Ene • Enone enolate+Alkyl-X • Alkyl-X+Enolate • Enone+Li-R • Li-Me+Ketone • Cationic cyclization • Ketone enamine+Alkyl-X • Alkyl-X+Enamine • Claisen acylation, carbonate • CarboxEster enolate+Carbonate • MalonicEster → Allyl-OH • Allyl-OH → EnoateEster • Allylic oxidation → Allyl-OH •
Reagents: NaH • MeLi • Formic acid • 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 •

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