acetic acid in water T=25°C; 24 h;

sodium methylate in methanol T=20°C; Hydrolysis; 4 h;

1: acetyl chloride, pyridine 2: 16 percent / pyridine / 1,2-dichloro-ethane / -5 - 0 °C 3: 97.6 percent / pyridine, Ac2O, CrO3 / CH2Cl2 / 0.08 h 4: 31.2 percent / diethyl ether / 0.17 h / 0 °C 5: 63 percent / N-methylimidazole / 0.5 h / 150 °C 6: SnCl4 / 1,2-dichloro-ethane / 15 h / Heating 7: 1.) CF3SO3SiMe3, 2.) NaOMe, MeOH / 1.) 1,2-dichloroethane, 15 min, reflux, 2.) 1,2-dichloroethane, 20 deg C, 1 h 8: 95 percent / pyridine / 0.17 h / Heating 9: 1.) SOCl2, 2.) NH3, methanol / 1.) reflux, 2 min, 2.) 20 deg C, 24 h View Scheme

1: 83 percent / diethyl ether / 0.17 h / 0 °C 2: 54 percent / N-methylimidazole / 0.5 h / 150 °C 3: 1.) CF3SO3SiMe3, 2.) NaOMe, MeOH / 1.) 1,2-dichloroethane, 15 min, reflux, 2.) 1,2-dichloroethane, 20 deg C, 1 h 4: 95 percent / pyridine / 0.17 h / Heating 5: 1.) SOCl2, 2.) NH3, methanol / 1.) reflux, 2 min, 2.) 20 deg C, 24 h View Scheme

1: 97.6 percent / pyridine, Ac2O, CrO3 / CH2Cl2 / 0.08 h 2: 31.2 percent / diethyl ether / 0.17 h / 0 °C 3: 63 percent / N-methylimidazole / 0.5 h / 150 °C 4: SnCl4 / 1,2-dichloro-ethane / 15 h / Heating 5: 1.) CF3SO3SiMe3, 2.) NaOMe, MeOH / 1.) 1,2-dichloroethane, 15 min, reflux, 2.) 1,2-dichloroethane, 20 deg C, 1 h 6: 95 percent / pyridine / 0.17 h / Heating 7: 1.) SOCl2, 2.) NH3, methanol / 1.) reflux, 2 min, 2.) 20 deg C, 24 h View Scheme

1: 97.6 percent / pyridine, Ac2O, CrO3 / CH2Cl2 / 0.08 h 2: 83 percent / diethyl ether / 0.17 h / 0 °C 3: 54 percent / N-methylimidazole / 0.5 h / 150 °C 4: 1.) CF3SO3SiMe3, 2.) NaOMe, MeOH / 1.) 1,2-dichloroethane, 15 min, reflux, 2.) 1,2-dichloroethane, 20 deg C, 1 h 5: 95 percent / pyridine / 0.17 h / Heating 6: 1.) SOCl2, 2.) NH3, methanol / 1.) reflux, 2 min, 2.) 20 deg C, 24 h View Scheme

1: 72 percent / NaI; Et3N / acetonitrile; pentane / 4 h / 40 °C 2: 60 percent / ZnCl2 / ethyl acetate / 1 h / 20 °C 3: 81 percent / sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 1 h / 0 - 5 °C 4: (-)-DIPT; Ti(Oi-Pr)4; t-BuOOH / CH2Cl2 / 8 h / -20 °C 5: 87 percent / Ti(Oi-Pr)4 / benzene / 2 h / 80 °C 6: 84 percent / HCl / ethanol / 0.5 h / 20 °C 7: 76 percent / pyridine / 3 h / 0 °C 8: 64 percent / trimethylsilyl triflate / acetonitrile / 16 h / 20 °C 9: 22 percent / CH3ONa / methanol / 4 h / 20 °C View Scheme

1: 60 percent / ZnCl2 / ethyl acetate / 1 h / 20 °C 2: 81 percent / sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 1 h / 0 - 5 °C 3: (-)-DIPT; Ti(Oi-Pr)4; t-BuOOH / CH2Cl2 / 8 h / -20 °C 4: 87 percent / Ti(Oi-Pr)4 / benzene / 2 h / 80 °C 5: 84 percent / HCl / ethanol / 0.5 h / 20 °C 6: 76 percent / pyridine / 3 h / 0 °C 7: 64 percent / trimethylsilyl triflate / acetonitrile / 16 h / 20 °C 8: 22 percent / CH3ONa / methanol / 4 h / 20 °C View Scheme

1: 95 percent / Zn, TiCl4 / tetrahydrofuran; CH2Cl2 / 20 °C 2: 78 percent / CH3COOH / H2O / 24 h / 25 °C View Scheme

1: 54 percent / N-methylimidazole / 0.5 h / 150 °C 2: 1.) CF3SO3SiMe3, 2.) NaOMe, MeOH / 1.) 1,2-dichloroethane, 15 min, reflux, 2.) 1,2-dichloroethane, 20 deg C, 1 h 3: 95 percent / pyridine / 0.17 h / Heating 4: 1.) SOCl2, 2.) NH3, methanol / 1.) reflux, 2 min, 2.) 20 deg C, 24 h View Scheme