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Total synthesis of Chrysochlamic Acid:
Reference: Maloney, D. J.; Hecht, S. M. Org. Lett. 2005, 6, 4297 DOI
Keywords: CarboxEster -> Alkyl-OH • O-H -> O-SiEt3 • Alkyl-OH -> Aldehyde • O-SiEt3 -> O-H • CarboxEster -> CarboxAcid • Pd/B-Vinyl+Alkyl-I • Suzuki coupling • Pd/Zn-Vinyl+Alkyl-I • Negishi coupling • Sharpless epoxidation • HWE -> EnoateEster • Epoxide reduction • Li/I -> Li-Vinyl • Li/I -> Li-Vinyl • Li-Vinyl -> Zn-Vinyl • Carboalumination Alkyne • Aryl-OMe -> Aryl-OH • Alkyl-OH -> Alkyl-I • Finkelstein reaction • Wittig-carboxymethyl -> EnoateEster •
Reagents: P(O)(OEt)2CH2-CO2R • NaH • AlHiBu2 • Hydroperoxide, tbutyl • Ti(OiPr)4 • AlH2(OR)2-Na+ • MeSO2Cl, NEt3 • Iodide, sodium • HSiEt3 • BuLi(tert) • Pd(PPh3)4 • Fluoride, Bu4N+ • AlMe3 • ZrCp2Cl2 • Dess-Martin • Ph3P=C(Me)-CO2R • BuLi(tert) • 9-BBN-OMe • PdCl2(dppf) • Fluoride, Bu4N+ • Carbonate, potassium • Ceric ammonium nitrate • Sulfide, sodium •

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