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Total synthesis of β-Elemenone:
Reference: Majetich, G.; Grieco, P. A.; Nishizawa, N. J. Org. Chem. 1977, 42, 2327. DOI
Keywords: Alkyl-OH→ Alkyl-SeR • Ketal → Ketone • Dieckmann • CarboxEster → CarboxAcid • Selenoxide-Ei → Ene • ConjReduct Enone • EnolPhosphate → Vinyl-H • Ketone → Alkene • Ketone enolate+CS2 • Decarboxylation β-keto acid • KetoEster enolate+Alkyl-X • Alkyl-X+Enolate • Cyclohexanone • Ozonolysis • Cu-Me+Enone-β-X • Enone-β-X+Cu-R • ConjAdd Cu-R • Knoevenagel condensation • Decarboxylation malonic • Robinson annulation, ketone • Ketone enolate+Enone • Cyclohexenone • CarboxAcid(dithio) → Ketene acetal(thio) • Fischer esterification • CarboxAcid → CarboxEster • Ketone → Ketal • Ketone → EnolPhosphate • Aldehyde → Alkyl-OH •
Reagents: Li°/NH3 • LiNiPr2 • P(O)(OR)2Cl • Li°/EtNH2 • O3 • BH4-Na+ • Selenocyanate, o-nitrophenyl • PBu3 • H2O2 • CS2 • LiCuMe2 • HCl, MeOH • Glycol • NaOMe • MeI • Hydroxide, potassium • Malonate • Ethyl vinyl ketone • NaH •

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