1: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 24 deg C, 1 h 2: hexane; methanol / 14 h / Heating 3: hydrochloric acid / ethanol 4: 93 percent / hydrogen / 5 percent palladium on carbon / ethanol / 0.25 h / 775.7 Torr View Scheme

1: 91 percent / N-bromosuccinimide, benzoylperoxide / CCl4 / Heating; Irradiation 2: sodium cyanoborohydride, hexamethylphosphoramide / 10 h / 70 °C 3: 93 percent / potassium carbonate / methanol / 2 h / 22 °C 4: 81 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 5: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 24 deg C, 1 h 6: hexane; methanol / 14 h / Heating 7: hydrochloric acid / ethanol 8: 93 percent / hydrogen / 5 percent palladium on carbon / ethanol / 0.25 h / 775.7 Torr View Scheme

1: 93 percent / potassium carbonate / methanol / 2 h / 22 °C 2: 81 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 3: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 24 deg C, 1 h 4: hexane; methanol / 14 h / Heating 5: hydrochloric acid / ethanol 6: 93 percent / hydrogen / 5 percent palladium on carbon / ethanol / 0.25 h / 775.7 Torr View Scheme

1: 49 percent / trifluoroacetic acid / 0.25 h / Heating 2: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 24 deg C, 1 h 3: hexane; methanol / 14 h / Heating 4: hydrochloric acid / ethanol 5: 93 percent / hydrogen / 5 percent palladium on carbon / ethanol / 0.25 h / 775.7 Torr View Scheme

1: sodium cyanoborohydride, hexamethylphosphoramide / 10 h / 70 °C 2: 93 percent / potassium carbonate / methanol / 2 h / 22 °C 3: 81 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 4: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 24 deg C, 1 h 5: hexane; methanol / 14 h / Heating 6: hydrochloric acid / ethanol 7: 93 percent / hydrogen / 5 percent palladium on carbon / ethanol / 0.25 h / 775.7 Torr View Scheme