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Total synthesis of Jiadifenolide:
Reference: Paterson, I.; Xuan, M.; Dalby, S. M. Angew. Chem. Int. Ed. 2014, 53, 7286–7289. DOI
Keywords: Enone → Allyl-OH • O-H → O-SiMe2tBu • O-H → O-C(O)R • O-H → O-SiEt3 • O-SiEt3 → O-H • Alkyl-OH → Ketone • Ketone → EnolSilane • O-H → O-SiEt3 • Alkyl-OH → KetoEster • O-SiEt3 → O-H • HWE → EnoateEster • Pinacol • Epoxidation, peracid • Henbest • EnoateEster → Allyl-OH • CarboxEster → Alkyl-OH • Alkyl-OH → Aldehyde • Alkyl-OH → Ketone • Aldol-B • Radical cyclization(Ketyl) • EnolSilane → Ketone-α-OH • Ketone → Alkyl-OH • Alkene → Diol-1,2 •
Reagents: BH4-Na+ • CeCl3 • Perbenzoic acid, 3-chloro • BF3·OEt2 • NaH • AlH4-Li+ • Acetic anhydride • DMAP • LiNiPr2 • AlH4-Li+ • HCl • DMSO, (COCl)2 (Swern) • BOTfBu2 • SiEt3-Cl • SmI2 • TsOH·Py • CrO3Cl·PyH (PCC) • SiMe3-OTf • NEt3 • NMO • SiEt3-Cl • OsO4, NMO • RuO4-Pr4N+, NMO • HF·Py •

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