Total synthesis of Jiadifenolide (Zhang):
| Reference: | Shen, J.; Li, L.; Pan, Z.; Wang, Y.; Li, J.; Wang, K.; Wang, X.; Zhang, Y.; Hu, T.; Zhang, Y.; Org. Lett. 2015, 17, 5480–5483. DOI |
| Reactions: | 1+4 annulation • Ether-5 • Propellane(433)-oxa • CarboxEster → EnolBorane • O-H → O-C(O)R • Ozonolysis • Ketyl+Enone • Cyclohexane • Bicyclo(430) • Li-Diazomethane+Aldehyde • CompE+-Aldehyde/CarboxEster+M-R • Dehydroacetoxylation → Ene • CarboxEster → Alkyl-OH • Protecting group - Ketone • Hydrogenation Diene • CompRed-Alkene/Alkene+H2 • Aldol-BR2 → Aldol • Lactone enolate+Aldehyde • CompE+-Aldehyde/Ketone+enolate • Lactone → EneLactone • Selenoxide-Ei → EneLactone • Epoxidation, dioxirane • Ether oxidation → CarboxEster • Ketone-α-OR → Ketone-1,2-di • Epoxide → Diol • Alkyl-OH → Aldehyde • Acetoacetic ester synthesis • KetoEster enolate+Alkyl-X • Selenide → Selenoxide • |
| Reagents: | Hydroxide, lithium • RuCl3 • Periodate, sodium • Sulfide, sodium • KN(SiMe3)2 • SePh-Br • Diazomethane, silyl • BuLi(n) • Chloride, lithium • DMSO, (COCl)2 (Swern) • SmI2 • AlHiBu2 • H2, Pt • Allyl-Br • Carbonate, cesium • O3; PPh3 • NEt3 • B(OTf)Bu2 • Acetic anhydride, DMAP • LiNiPr2 • NEt3 • Dioxirane • Perbenzoic acid, 3-chloro • |