Total synthesis of α-Vetivone:
| Reference: | Marshall, J. A.; Faubl, H.; Warne, T. M. Chem. Commun. 1967, 753. DOI |
| Reactions: | Dieckmann • CarboxEster enolate+CarboxEster • Cyclohexanone • Robinson annulation, ketoester • KetoEster enolate+Enone • Cyclohexenone • Bicyclo(440) • O-H → O-SO2Me • Malonic Ester Synthesis • CarboxEster enolate+Alkyl-X • Allyl-X+Enolate • Alkyl-OH → Alkyl-H • Decarboxylation malonic • Allyl-OH → Allyl-Br • Radical cyclization(Alkyl) • CarboxEster → Alkyl-OH • CarboxAcid → CarboxEster • Fischer esterification • Ketone → Ketal • CarboxEster → Alkyl-OH • Ketal → Enone • Alkene isomerization • |
| Reagents: | Allyl-Br • Methyl vinyl ketone • Glycol • AlH4-Li+ • PBr3 • Malonate • HOMe (react) • NaH • AlH4-Li+ • Sulfonyl chloride, methane, NEt3 • Li°/NH3 • AlH4-Li+ • |