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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 • Alkyl-X+Enolate • Claisen acylation, carbonate • Ketone enolate+Carbonate • Ketone → Ketone-α-OR • Enone enolate+Alkyl-X • Alkyl-X+Enolate • 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, H2O • 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) • HMPA (solvent) •

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