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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: Fischer esterification • CarboxEster -> Alkyl-OH • Stobbe condensation • CarboxEster enolate+Ketone • Robinson annulation, ketoester • Ketoester enolate+EnoateEster • Allyl-OH -> Allyl-Cl • Finkelstein reaction • Li-Me+Ketone • Enone+Li-R • Enone-β-OR -> Enone • Stork-Danheiser • Baldwin rules • Ketone -> Enolether • Enone enolate dialkylation, spiro • Mechanism •
Reagents: KOtBu • Acetone (react) • AlH3 • MeLi • MeSO2Cl • Chloride, lithium • HMPA (solvent) • NaOEt • MeLi • Crotonate • Allyl-Cl • LiNiPr2, HMPA •

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