image

Total synthesis of Citreoviral:
Reference: Williams, D. R.; White, F. H. J. Org. Chem. 1987, 52, 5067
Keywords: O-H -> O-SEM --- Ozonolysis --- Ozonolysis --- O-SEM -> O-H --- O-C(O)R -> O-H --- EnoateEster -> Allyl-OH --- Allyl-OH -> Enal --- Mg-Vinyl+Ketone --- Mg-Vinyl+Aldehyde --- Iodoetherification --- Ether-5 --- Dehydroiodination -> Allyl-OR --- Wittig-carboxymethyl -> EnoateEster
Reagents: Vinyl-MgX --- MEM-Cl --- Vinyl-MgX --- I2, NaHCO3 --- Benzoyl chloride --- DBU --- O3 --- Ph3P=C(Me)-CO2R --- ZnBr2 --- AlHiBu2 --- MnO2

Syntheses Home