1: 99 percent / p-toluenesulfonic acid / 2 h / Ambient temperature 2: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature 3: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature 4: 83 percent / sodium borohydride / methanol / 2 h / 0 °C View Scheme

1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature 2: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature 3: 83 percent / sodium borohydride / methanol / 2 h / 0 °C View Scheme

1: 1.) diethyl(methoxy)borane, 2.) sodium borohydride / 1.) THF, methanol, RT, 15 min, 2.) THF, methanol, a) -78 deg C, 4 h, b) from -78 deg C to RT, 8 h 2: 99 percent / p-toluenesulfonic acid / 2 h / Ambient temperature 3: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature 4: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature 5: 83 percent / sodium borohydride / methanol / 2 h / 0 °C View Scheme

1: 60 percent / DIBAL / tetrahydrofuran; hexane / 4 h / -78 °C 2: 1.) diethyl(methoxy)borane, 2.) sodium borohydride / 1.) THF, methanol, RT, 15 min, 2.) THF, methanol, a) -78 deg C, 4 h, b) from -78 deg C to RT, 8 h 3: 99 percent / p-toluenesulfonic acid / 2 h / Ambient temperature 4: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature 5: 85 percent / sodium metaperiodate, water / diethyl ether / 3 h / Ambient temperature 6: 83 percent / sodium borohydride / methanol / 2 h / 0 °C View Scheme

1: 81 percent / H(1+) 2: 1.) Bu3SnLi / 2.) Pd(PPh3)4 3: 1.) O3, 2.) NaBH4 / 1.) methanol View Scheme

1: 60 percent / Et2BOMe, NaBH4 2: 81 percent / H(1+) 3: 1.) Bu3SnLi / 2.) Pd(PPh3)4 4: 1.) O3, 2.) NaBH4 / 1.) methanol View Scheme

1: 1.) Bu3SnLi / 2.) Pd(PPh3)4 2: 1.) O3, 2.) NaBH4 / 1.) methanol View Scheme

1: 74 percent / NaH, n-BuLi / 20 h / -78 °C 2: 60 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 4 h / -78 °C 3: 76 percent / Et2BOMe, NaBH4 / tetrahydrofuran; methanol / -78 deg C to RT, 12 h 4: 98 percent / p-TsOH / 2 h / Ambient temperature 5: 99 percent / (n-Bu)4NF / tetrahydrofuran / 3 h / Ambient temperature 6: 85 percent / NaIO4 / diethyl ether; H2O / 2 h / Ambient temperature 7: NaBH4 / methanol / 0 °C View Scheme

sodium tetrahydroborate; ozone 1.) methanol; Yield given. Multistep reaction;

1.1: triethylamine / dichloromethane / 1 h / 0 - 5 °C 2.1: sodium hydroxide; water / methanol / 40 °C 2.2: pH 2 - 4 3.1: 1,1'-carbonyldiimidazole / ethyl acetate / 3 h / 0 - 30 °C 3.2: 20 - 25 °C 4.1: potassium carbonate / acetonitrile / 70 °C 4.2: 15 h / 0 - 25 °C 5.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -70 - -10 °C 6.1: sulfuric acid / acetonitrile / 3 h / 50 - 60 °C View Scheme