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Total synthesis of Jiadifenin:
Reference: Cho, Y. S.; Carcache, D. A.; Tian, Y.; Li, Y.-M.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 14358–14359. DOI
Keywords: O-H -> O-SiMe2tBu • Li-Phosphonate+CarboxEster • HWE -> Enone • Ketal -> Ketone • O-SiMe2tBu -> O-H • O-H -> O-C(O)OR • Lactone-5 • Ketone -> Alkyl-OH • Aldehyde -> CarboxAcid • Lactone-6 • Lactone-6 • Ketone -> Alkyl-OH • Allyl-OH -> Enone • Ketone enolate+Me-I • Ketone enolate+Aldehyde • Aldol-Na -> Aldol • Ketone enolate+Alkyl-X • Bromoacetate+Enolate • Claisen acylation, carbonate • Ketone enolate+Carbonate • Ketone -> Ketone-α-OR • Enone enolate+Alkyl-X • Ozonolysis • CompOx-Alkene/Enone+O3 • Lactone -> Lactone-α-OH • CarboxEster enolate oxidation • Oxaziridine+Enolate •
Reagents: LiN(SiMe3)2 • MeI • Hydroxide, potassium • Formaldehyde • SiMe2tBu-OTf • LiN(SiMe3)2 • Allyl-Br • LiNiPr2 • Bromoacetate • HMPA (solvent) • P(O)(OMe)2CH2-Li • NaH • HCl • O=C(OR)Cl • NaH • Perbenzoic acid, 3-chloro • BH4-Na+ • LiNiPr2 • MeI • O3 • Sudan 7B Red • CrO3, H2SO4 (Jones) • BH4-Na+, CeCl3 • NaN(SiMe3)2 • Oxaziridine • CrO3, H2SO4 (Jones) •

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