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Total synthesis of β-Vetivone:
Reference: Stork, G.; Danheiser, R.L.; Ganem, B. J. Am. Chem. Soc., 1973, 95, 3414. DOI
Keywords: O-H → O-SO2R • Alkyl-X → Alkyl-Cl • Finkelstein reaction • Stobbe condensation • CarboxEster enolate+Ketone • Robinson annulation, ketoester • KetoEster enolate+EnoateEster • Allyl-OH → Allyl-Cl • Li-Me+Ketone • Enone+Li-R • Enone-β-OR → Enone • Stork-Danheiser • Baldwin rules • Ketone → EnolEther • Enone enolate dialkylation, spiro • Cyclopentane • Mechanism • CarboxEster → Alkyl-OH • EnolEther → Enone • Decarboxylation β-keto acid • Fischer esterification • CarboxAcid → CarboxEster •
Reagents: Succinate • KOtBu • Acetone (react) • AlH3 • MeLi • Sulfonyl chloride, methane • Chloride, lithium • HMPA (solvent) • Acetoacetate • NaOEt • MeLi • Crotonate • Allyl-Cl • LiNiPr2, HMPA • HMPA (solvent) • Allyl-Cl •

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