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Total synthesis of α-Vetivone:
Reference: Marshall, J. A.; Faubl, H.; Warne, T. M. Chem. Commun. 1967, 753. DOI
Keywords: CarboxEster → Alkyl-OH • Fischer esterification • CarboxAcid → CarboxEster • Dieckmann • CarboxEster enolate+CarboxEster • Robinson annulation, ketoester • Ketoester enolate+Enone • CarboxEster → Alkyl-OH • O-H → O-SO2R • Ketal → Enone • Malonic Ester Synthesis • CarboxEster enolate+Alkyl-X • Alkyl-X+Enolate • Alkyl-OH → Alkyl-H • Decarboxylation • Allyl-OH → Allyl-Br • Radical cyclization(Alkyl) •
Reagents: Allyl-Br • Methyl vinyl ketone • Glycol • AlH4-Li+ • PBr3 • Malonate • NaH • AlH4-Li+ • Sulfonyl chloride, methane, NEt3 • Li°/NH3 • AlH4-Li+

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