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Total synthesis of Jiadifenolide:
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
Keywords: Selenide → Selenoxide • 4+1 annulation • O-H → O-SO2R • Acetoacetic ester synthesis • KetoEster enolate+Alkyl-X • O-H → O-C(O)R • Ozonolysis • Ketyl+Enone • Li-Diazomethane+Aldehyde • CompE+-Aldehyde/CarboxEster+M-R • Dehydroacetoxylation → Ene • CarboxEster → Alkyl-OH • Hydrogenation Diene • CompRed-Alkene/Alkene+H2 • Aldol-B • Lactone enolate+Aldehyde • CompE+-Aldehyde/Ketone+enolate • Lactone → EneLactone • Selenoxide-Ei → EneLactone • Epoxidation, dioxirane • Ether oxidation →CarboxEster • Ketone-α-OH → Ketone-1,2-di • Epoxide → Diol •
Reagents: Hydroxide, lithium • RuCl3 • Periodate, sodium • Sulfide, sodium • KN(SiMe3)2 • SePh-Br • Perbenzoic acid, 3-chloro • Diazomethane, silyl • BuLi(n) • Chloride, lithium • NEt3 • SmI2 • AlHiBu2 • H2, Pt • Allyl-Br • Carbonate, cesium • O3 • PPh3 • NEt3 • BOTfBu2 • Acetic anhydride, DMAP • NEt3 • Dioxirane •

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