orthoacetic acid trimethyl ester; chloro-trimethyl-silane; potassium carbonate in methanol

1: 100 percent / H2, conc. HCl / Pt/C / H2O / 264 h / Ambient temperature 2: 98 percent / 4M NaOH / Ambient temperature 3: (COCl)2, DMSO, Et3N / tetrahydrofuran / 0.5 h / -35 - 20 °C 4: 1.) nBuLi / 1.) THF, hexane, room temperature, 30 min, 2.) -78 deg C -> room temperature, 1 h 5: I2 / CHCl3 / 192 h / Irradiation 6: 72 percent / Ad-mix-α, CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 1.) 0 deg C, 7 h, 2.) room temperature, 17 h 7: 1.) CH3C(OCH3)3, TMSCL, 2.) K2CO3 / 1.) CH2Cl2, room temperature, 3 h, 2.) MeOH, room temperature, 1 h View Scheme

1: 1.) nBuLi / 1.) THF, hexane, room temperature, 30 min, 2.) -78 deg C -> room temperature, 1 h 2: I2 / CHCl3 / 192 h / Irradiation 3: 72 percent / Ad-mix-α, CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 1.) 0 deg C, 7 h, 2.) room temperature, 17 h 4: 1.) CH3C(OCH3)3, TMSCL, 2.) K2CO3 / 1.) CH2Cl2, room temperature, 3 h, 2.) MeOH, room temperature, 1 h View Scheme

1: 72 percent / Ad-mix-α, CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 1.) 0 deg C, 7 h, 2.) room temperature, 17 h 2: 1.) CH3C(OCH3)3, TMSCL, 2.) K2CO3 / 1.) CH2Cl2, room temperature, 3 h, 2.) MeOH, room temperature, 1 h View Scheme

1: 98 percent / NaOH / 0 °C 2: (COCl)2, Et3N / dimethylsulfoxide / -78 deg C to r.t. 3: 2.) I2 / 1.) THF, -78 deg C; 2.) CHCl3, r.t., irradiation 4: 72 percent / AD-mix-α, CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C 5: 87 percent / trimethylorthoacetate, trimethylsilylchloride, K2CO3 / methanol View Scheme

1: 1.) BH3*SMe2; 2.) H2; Pt/C / 2.) 1 atm 2: 98 percent / NaOH / 0 °C 3: (COCl)2, Et3N / dimethylsulfoxide / -78 deg C to r.t. 4: 2.) I2 / 1.) THF, -78 deg C; 2.) CHCl3, r.t., irradiation 5: 72 percent / AD-mix-α, CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C 6: 87 percent / trimethylorthoacetate, trimethylsilylchloride, K2CO3 / methanol View Scheme

1: 98 percent / NaOH / 0 °C 2: (COCl)2, Et3N / dimethylsulfoxide / -78 deg C to r.t. 3: 2.) I2 / 1.) THF, -78 deg C; 2.) CHCl3, r.t., irradiation 4: 72 percent / AD-mix-α, CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 0 °C 5: 87 percent / trimethylorthoacetate, trimethylsilylchloride, K2CO3 / methanol View Scheme