Total synthesis of Citreoviral:
| Reference: | Williams, D. R.; White, F. H. J. Org. Chem. 1987, 52, 5067 DOI |
| Reactions: | Mg-Vinyl+Ketone • Mg-Vinyl+Aldehyde • Felkin-Anh • Dehydrohalogenation → Allyl-OR • Wittig-carboxymethyl → EnoateEster • Felkin-Anh Chelation • Iodoetherification • Ether-5 • Ozonolysis • O-MEM → O-H • EnoateEster → Allyl-OH • Allyl-OH → Enal • Ozonolysis • O-H → O-C(O)R • O-H → O-MEM • |
| Reagents: | Vinyl-MgX • O3; Me2S • DBU • O3 • PPh3=C(Me)-CO2R • ZnBr2 • AlHiBu2 • MnO2 • I2 • Benzoyl chloride • MEM-Cl • NEtiPr2 • |