image

Total synthesis of Griseofulvin:
Reference: Pirrung, M. C.;Brown, W. L.; Rege, S.; Laughton, P. J. Am. Chem. Soc. 1991, 113, 8561. DOI
Keywords: O-H -> O-C(O)R • Regitz diazo transfer • CarboxEster -> CarboxAcid • Vinyl-OH -> Vinyl-OMe • Fries rearrangement • Claisen acylation, Mander • Ketone enolate+Mander • Aryl-H -> Aryl-Cl • Mitsunobu -> Ether • Aryl-OH -> Aryl-OR • Ozonolysis • Wittig-carboxymethyl -> EnoateEster • CompE+-Aldehyde/Ketone+Wittig • Curtius • C-CO2H -> C-N • Claisen acylation, ester • Ketone enolate+CarboxEster • Ether-5 • 2,3-Sigmatropic Ylide-O • Oxonium ylide • Ether-5 • Diazoketone • Mechanism •
Reagents: SO2Cl2 • Acetic anhydride, Py • AlCl3 • PPh3, DIAD • LiN(SiMe3)2 • O=C(OR)CN • NEt3 • O3 • Me2S • PPh3=C(Me)-CO2R • Acetic acid, trifluoro • Azide, diphenylphosphoryl • HCl, H2O • NaOMe • Diazomethane • Rh2(OPiv)4

Syntheses Home