Total synthesis of Acorenone:
| Reference: | Trost, B. M.; Hiroi, K.; Holy, H J. Am. Chem. Soc. 1975, 97, 5873 DOI |
| Reactions: | Ketone → Ketal(thio) • Claisen acylation, formate • Ketone enolate+CarboxEster • Cu-Me+Enone-β-X • ConjAdd-Elimination • Enone-β-X+Cu-R • ConjAdd Cu-Me • Sulfonium ylide+Ketone • Epoxidation ylide • Corey-Chaykowsky • Cyclobutane • Spiro(43) • Claisen acylation, formate • Ketone enolate+CarboxEster • Claisen-Retro • Lactone → Alkyl-OH • Li-Me+Lactone • Lactone+Li-R • Aldol-K → Enone • Spiro(54) • Ketone → Ketone-α-SR • Enone+Li-R • Li-Me+Ketone • EneSulfide → Ketone • Alkyl-OH → CarboxAcid • Lactone-6 • Alkyl-OH → Aldehyde • CompOx-Alkyl-OH/Sulfide+DMSO • Ketal(thio) → Ketone • Dehydration → Ene • Enol → EnolEster • |
| Reagents: | Formate, ethyl • NaOMe • Acetic anhydride • Me-Cuprate • Me2S=CH2 • LiBF4 • Formate, ethyl • NaH • TsOH • AlHiBu2 • CrO3 • Me-Li • DMSO, Py·SO3 (Parikh-Doering) • HgCl2 • Hydroxide, potassium • LiNiPrCy • Disulfide, phenyl • Me-Li • TsOH • HgCl2 • Hydroxide, potassium • |