image

Total synthesis of Acorenone:
Reference: Trost, B. M.; Hiroi, K.; Holy, H J. Am. Chem. Soc. 1975, 97, 5873 DOI
Keywords: Enol → EnolAcetate • Alkyl-OH → CarboxAcid • Lactone-6 • Ketone → Ketal(thio) • Alkyl-OH → Aldehyde • Ketal(thio) → Ketone • Dehydration → Ene • Claisen acylation, formate • Ketone enolate+CarboxEster • Cu-Me+Enone-β-X • ConjAdd-Elimination • Enone-β-X+Cu-R • ConjAdd Cu-R • Sulfonium ylide+Ketone • Corey-Chaykowsky • Claisen acylation, formate • Ketone enolate+CarboxEster • Claisen-Retro • Lactone → Lactol • Li-Me+Lactone • Lactone+Li-R • Aldol-K → Enone • Ketone → Ketone-α-SR • Enone+Li-R • Li-Me+Ketone • EneSulfide → Ketone •
Reagents: Formate, ethyl • NaOMe • Acetic anhydride • LiCuMe2 • Hydroxide, potassium • LiBF4 • Formate, ethyl • NaH • TsOH • AlHiBu2 • CrO3 • MeLi • DMSO, Py·SO3 (Parikh-Doering) • HgCl2 • Hydroxide, potassium • LiNiPrCy • Disulfide, phenyl • MeLi • TsOH • HgCl2

Syntheses Home