1: 1.) NaBH4 / 1.) ethanol, r.t., 15 min; 2.) ethanol, r.t., 1.5 h 2: 65 percent / trifluoroacetic acid / CH2Cl2 / 0.25 h / 0 °C 3: 46.2 percent / 30percent H2O2 / methanol / 0.17 h / 0 °C 4: 93 percent / CCl4 / 16 h / Heating 5: 88.5 percent / thionyl chloride, pyridine / CH2Cl2 / 0.08 h / 0 °C 6: 90.6 percent / 1N KOH / methanol / 4 h / Ambient temperature 7: 12.1 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 68 percent / Li2CuCl4 / tetrahydrofuran / 0 - 20 °C 2: 60 percent / Mn; 2,4,6-collidine; Me3SiCl / Cp2TiCl2 / tetrahydrofuran / 20 °C 3: 76 percent / DMAP / CH2Cl2 / 2 h / 20 °C 4: 77 percent / AIBN; HSnBu3 / benzene / 1 h / Heating View Scheme

1: 1.) NaBH4 / 1.) ethanol, r.t., 15 min; 2.) ethanol, r.t., 1.5 h 2: 65 percent / trifluoroacetic acid / CH2Cl2 / 0.25 h / 0 °C 3: 46.2 percent / 30percent H2O2 / methanol / 0.17 h / 0 °C 4: 93 percent / CCl4 / 16 h / Heating 5: 88.5 percent / thionyl chloride, pyridine / CH2Cl2 / 0.08 h / 0 °C 6: 90.6 percent / 1N KOH / methanol / 4 h / Ambient temperature 7: 27.4 percent / chromium trioxide-pyridine complex / 1 h / Ambient temperature 8: 39.1 percent / pyridine / 2.5 h / Heating View Scheme

1: 1.) selenium dioxide; 2.) PCC, molecular sieve 4A / 1.) camphorsulfonic acid / 1.) dioxane, 50 deg C; 2.) CH2Cl2, RT View Scheme

1: HIO4*2H2O / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C 2: NaBH4 / ethanol / 1 h / 0 °C 3: imidazole / dimethylformamide / 0 °C 4: K2CO3 / methanol / 1 h / 20 °C 5: 90 percent / Et3N / hexane / 24 h / 0 - 20 °C 6: tetrahydrofuran / 12 h / 0 - 20 °C 7: TBAF / tetrahydrofuran / 6 h View Scheme

1: HIO4*2H2O / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C 2: p-TsOH / toluene / 5 h / Heating 3: 65 percent / K2CO3 / methanol / 10 h 4: 97 percent / N-chlorosuccinimide-DMS / CH2Cl2 / 6 h / 0 °C 5: 86 percent / dimethylformamide / 5 h / 0 °C View Scheme

1,3-dimethyl-imidazolidin-2-one; toluene-4-sulfonic acid in dichloromethane T=20°C; 2 h; regioselective reaction;

1: HIO4*2H2O / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C 2: NaBH4 / ethanol / 1 h / 0 °C 3: imidazole / dimethylformamide / 0 °C 4: K2CO3 / methanol / 1 h / 20 °C 5: 90 percent / Et3N / hexane / 24 h / 0 - 20 °C 6: tetrahydrofuran / 12 h / 0 - 20 °C 7: TBAF / tetrahydrofuran / 6 h 8: Et3N / CH2Cl2 / 0 - 20 °C 9: 18-crown-6 / CH2Cl2 / 6 h / Heating View Scheme

1.1: HIO4*2H2O / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C 2.1: NaBH4 / ethanol / 1 h / 0 °C 3.1: imidazole / dimethylformamide / 0 °C 4.1: K2CO3 / methanol / 1 h / 20 °C 5.1: 90 percent / Et3N / hexane / 24 h / 0 - 20 °C 6.1: tetrahydrofuran / 12 h / 0 - 20 °C 7.1: TBAF / tetrahydrofuran / 6 h 8.1: Et3N / CH2Cl2 / 0 - 20 °C 9.1: 18-crown-6 / CH2Cl2 / 6 h / Heating 10.1: diethyl ether / -78 - 0 °C 10.2: aq. NH4Cl / diethyl ether / 0.17 h / 0 °C View Scheme

1: 85 percent / NaIO4 / dioxane; H2O / 24 h / Ambient temperature 2: 87 percent / Jones reagent / acetone 3: conc. H2SO4 / Ambient temperature View Scheme