Total synthesis of Chrysochlamic Acid:
| Reference: | Maloney, D. J.; Hecht, S. M. Org. Lett. 2005, 6, 4297 DOI |
| Reactions: | O-H → O-SO2Me • CompNu-O-H/O-H+RSO2X • Alkyl-X → Alkyl-I • Finkelstein reaction • Alkyl-OH → Aldehyde • Pd/B-Vinyl+Alkyl-X • Pd/Zn-Vinyl+Alkyl-I • Sharpless epoxidation • HWE → EnoateEster • Epoxide reduction • Li/I → Li-Alkyl • Li/I → Li-Vinyl • Alkyl-OH → Alkyl-I • Finkelstein reaction • Wittig-carboxymethyl → EnoateEster • Carboalumination Alkyne • Si-Alkynyl → H-Alkynyl • Al-Vinyl → I-Vinyl • Quinone synthesis • Quinone → Hydroquinone • Li-R → B-R • O-H → O-SiEt3 • CarboxEster → Alkyl-OH • Li-R → Zn-R • CarboxEster → CarboxAcid • |
| Reagents: | P(O)(OR)2CH2-C(O)OR' • NaH • AlHiBu2 • Hydroperoxide, tbutyl - Ti • Epoxide • Sulfonyl chloride, methane, NEt3 • Iodide, sodium • SiEt3-OTf • BuLi(tert) • Pd(PPh3)4 • Alkynyl-SiR3 • Fluoride, R4N+ • AlMe3 • ZrCp2Cl2 • Vinyl-I • Dess-Martin • PPh3=C(Me)-CO2R • BuLi(tert) • B(OMe)BBN • PdCl2(dppf) • Fluoride, R4N+ • Carbonate, potassium • Ceric ammonium nitrate • Dithionite, sodium • I2 • Vinyl-Al • AlH2(OR)2-Na+ • ZnBr2 • Alkyl-BR2 • Tartrate, diethyl • |