1: 1.) boron trichloride / 1.) dichloromethane, -78 deg C, 1 h, 2.) methanol, - 78 deg C -> room temperature 2: 51 mg / H2 / 5percent Pd-C / ethyl acetate 3: 7 percent / sodium borohydride / methanol / 3 h View Scheme

1: 96 percent / toluene-p-sulphonic acid / acetone; H2O / 20 h / 20 °C 2: 87 percent / aqueous potassium hydroxide / methanol 3: 1.) boron trichloride / 1.) dichloromethane, -78 deg C, 1 h, 2.) methanol, - 78 deg C -> room temperature 4: 51 mg / H2 / 5percent Pd-C / ethyl acetate 5: 7 percent / sodium borohydride / methanol / 3 h View Scheme

1: 1.) di-isobutylaluminium hydride, 2.) aqueous acetic acid / 1.) toluene 2: 96 percent / toluene-p-sulphonic acid / acetone; H2O / 20 h / 20 °C 3: 87 percent / aqueous potassium hydroxide / methanol 4: 1.) boron trichloride / 1.) dichloromethane, -78 deg C, 1 h, 2.) methanol, - 78 deg C -> room temperature 5: 51 mg / H2 / 5percent Pd-C / ethyl acetate 6: 7 percent / sodium borohydride / methanol / 3 h View Scheme

1: 85 percent / lithium 1,1-dimethylethanethiolate / hexamethylphosphoric acid triamide / 2 h / 70 °C 2: 51 mg / H2 / 5percent Pd-C / ethyl acetate 3: 7 percent / sodium borohydride / methanol / 3 h View Scheme

sodium tetrahydroborate in methanol 3 h;

1: 51 mg / H2 / 5percent Pd-C / ethyl acetate 2: 7 percent / sodium borohydride / methanol / 3 h View Scheme

1: 10percent KOH / methanol / 20 h / 20 °C 2: 85 percent / lithium t-butylthiolate / hexamethylphosphoric acid triamide / 2 h / 70 °C 3: 99 percent / H2 / Pd/C 4: sodium borohydride View Scheme

1: H2 / 5percent Pd-C / ethyl acetate 2: 91 percent / polyphosphoric acid / 2 h / 70 °C 3: 84 percent / potassium t-butoxide / 2-methyl-propan-2-ol; 1,2-dimethoxy-ethane / 50 h / 20 °C 4: 84 percent / n-butyl-lithium, diethylamine / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide 5: 1.) di-isobutylaluminium hydride, 2.) aqueous acetic acid / 1.) toluene, -78 deg C, 2.5 h, 2.) room temperature, 30 min 6: 98 percent / m-hydrochloric acid / tetrahydrofuran / 12 h 7: 92 percent / aqueous potassium hydroxide / methanol / 24 h / 20 °C 8: 85 percent / lithium 1,1-dimethylethanethiolate / hexamethylphosphoric acid triamide / 2 h / 70 °C 9: 51 mg / H2 / 5percent Pd-C / ethyl acetate 10: 7 percent / sodium borohydride / methanol / 3 h View Scheme

1: 85 percent / H2 / 5percent Pd-C / ethyl acetate / Ambient temperature 2: 7 percent / sodium borohydride / methanol / 3 h View Scheme

1: 82 percent / lithium 1,1-dimethylethanethiolate / hexamethylphosphoric acid triamide / 2 h / 70 °C 2: 85 percent / H2 / 5percent Pd-C / ethyl acetate / Ambient temperature 3: 7 percent / sodium borohydride / methanol / 3 h View Scheme