Total synthesis of Actinidiolide:
| Reference: | Rubottom, G. M.; Juve, H. D. Jr. J. Org. Chem. 1983, 48, 422. DOI |
| Reactions: | Enone → EnolSilane • Dehydrohalogenation → Enone • Ketone-α-Halo → Enone • CarboxEster enolate+Ketone • Aldol-Li → Aldol • Lactone-5 • Ketone → Ketone-α-Halo • Ketone enolate+Br2 • Dehydration → EneLactone • Ketone → EnolSilane • Enone → EnolSilane • Ketone → Ketone-α-OR • EnolSilane+peracid • Rubottom oxidation • EnolSilane → Ketone enolate • O-H → O-C(O)R • |
| Reagents: | LiNiPr2 • SiMe3-Cl • Me-Li • Br2 • LiNiPr2 • SiMe3-Cl • LiNiPr2 • SOCl2 • Bromide, lithium • Carbonate, lithium • DMF (solvent) • Perbenzoic acid, 3-chloro • HF·NEt3 • Acetic anhydride, DMAP • |