Total synthesis of β-Vetivone:
| Reference: | Stork, G.; Danheiser, R.L.; Ganem, B. J. Am. Chem. Soc., 1973, 95, 3414. DOI |
| Reactions: | 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 • Spiro(54) • Mechanism • CarboxEster → Alkyl-OH • EnolEther → Enone • Decarboxylation β-keto acid • Fischer esterification • CarboxAcid → CarboxEster • O-H → O-SO2Me • |
| Reagents: | Succinate • KOtBu • Acetone (react) • HOEt (react)} • AlH3 • Me-Li • Sulfonyl chloride, methane • Chloride, lithium • Acetoacetate • NaOEt • HOEt (react)} • Me-Li • Crotonate • Allyl-Cl • LiNiPr2, HMPA • Allyl-Cl • HMPA (solvent) • |