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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 • ArylO-Me → ArylO-H • Alkyl-OH → Alkyl-I • Finkelstein reaction • Wittig-carboxymethyl → EnoateEster •
Reagents: P(O)(OR)2CH2-CO2R • NaH • AlHiBu2 • Hydroperoxide, tbutyl • Ti(OiPr)4 • AlH2(OR)2-Na+ • Sulfonyl chloride, methane, NEt3 • Iodide, sodium • SiEt3-OTf • BuLi(tert) • Pd(PPh3)4 • Fluoride, R4N+ • AlMe3 • ZrCp2Cl2 • Dess-Martin • PPh3=C(Me)-CO2R • Vinyl-I • BuLi(tert) • B(OMe)-BBN • PdCl2(dppf) • Fluoride, R4N+ • Carbonate, potassium • Ceric ammonium nitrate • Dithionite, sodium • I2

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