1.1: 95 percent / tetrapropylammonium perruthenate(VII); 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 2.1: NaN(TMS)2 / diethyl ether; toluene / 1 h / 20 °C 2.2: 86 percent / diethyl ether; toluene / 2 h / 20 °C 3.1: BH3*THF / tetrahydrofuran / 3 h / -78 °C 3.2: 73 percent / aq. NaOH; H2O2 / 0.5 h / 0 °C 4.1: triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 3 h / 0 °C 5.1: 627 g / t-BuOK / dimethylsulfoxide / 3 h / 20 °C 6.1: 82 percent / 3-chloroperoxybenzoic acid; sodium bicarbonate / CH2Cl2 / 2 h / 20 °C 7.1: n-BuLi / 1,2-dimethoxy-ethane; hexane / 0.17 h / -78 °C 7.2: 45 percent / 1,2-dimethoxy-ethane; hexane / 1 h / -78 °C 8.1: 66 percent / Na-Hg; Na2HPO4 / methanol / 2.5 h / 20 °C 9.1: 100 percent / Jones reagent / acetone / 0.5 h / 20 °C 10.1: 100 percent / trifluoroacetic acid / CH2Cl2 / 1.5 h / 20 °C 11.1: 91 percent / NaBH3CN / acetonitrile / 0.5 h / 20 °C View Scheme

1.1: BH3*THF / tetrahydrofuran / 3 h / -78 °C 1.2: 73 percent / aq. NaOH; H2O2 / 0.5 h / 0 °C 2.1: triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 3 h / 0 °C 3.1: 627 g / t-BuOK / dimethylsulfoxide / 3 h / 20 °C 4.1: 82 percent / 3-chloroperoxybenzoic acid; sodium bicarbonate / CH2Cl2 / 2 h / 20 °C 5.1: n-BuLi / 1,2-dimethoxy-ethane; hexane / 0.17 h / -78 °C 5.2: 45 percent / 1,2-dimethoxy-ethane; hexane / 1 h / -78 °C 6.1: 66 percent / Na-Hg; Na2HPO4 / methanol / 2.5 h / 20 °C 7.1: 100 percent / Jones reagent / acetone / 0.5 h / 20 °C 8.1: 100 percent / trifluoroacetic acid / CH2Cl2 / 1.5 h / 20 °C 9.1: 91 percent / NaBH3CN / acetonitrile / 0.5 h / 20 °C View Scheme

1.1: DIBAL-H / diethyl ether; hexane / 1 h / -78 °C 2.1: 1.50 g / BF3*Et2O / CH2Cl2 / 12 h / -60 °C 3.1: 95 percent / tetrapropylammonium perruthenate(VII); 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 4.1: NaN(TMS)2 / diethyl ether; toluene / 1 h / 20 °C 4.2: 86 percent / diethyl ether; toluene / 2 h / 20 °C 5.1: BH3*THF / tetrahydrofuran / 3 h / -78 °C 5.2: 73 percent / aq. NaOH; H2O2 / 0.5 h / 0 °C 6.1: triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 3 h / 0 °C 7.1: 627 g / t-BuOK / dimethylsulfoxide / 3 h / 20 °C 8.1: 82 percent / 3-chloroperoxybenzoic acid; sodium bicarbonate / CH2Cl2 / 2 h / 20 °C 9.1: n-BuLi / 1,2-dimethoxy-ethane; hexane / 0.17 h / -78 °C 9.2: 45 percent / 1,2-dimethoxy-ethane; hexane / 1 h / -78 °C 10.1: 66 percent / Na-Hg; Na2HPO4 / methanol / 2.5 h / 20 °C 11.1: 100 percent / Jones reagent / acetone / 0.5 h / 20 °C 12.1: 100 percent / trifluoroacetic acid / CH2Cl2 / 1.5 h / 20 °C 13.1: 91 percent / NaBH3CN / acetonitrile / 0.5 h / 20 °C View Scheme

1.1: triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 3 h / 0 °C 2.1: 627 g / t-BuOK / dimethylsulfoxide / 3 h / 20 °C 3.1: 82 percent / 3-chloroperoxybenzoic acid; sodium bicarbonate / CH2Cl2 / 2 h / 20 °C 4.1: n-BuLi / 1,2-dimethoxy-ethane; hexane / 0.17 h / -78 °C 4.2: 45 percent / 1,2-dimethoxy-ethane; hexane / 1 h / -78 °C 5.1: 66 percent / Na-Hg; Na2HPO4 / methanol / 2.5 h / 20 °C 6.1: 100 percent / Jones reagent / acetone / 0.5 h / 20 °C 7.1: 100 percent / trifluoroacetic acid / CH2Cl2 / 1.5 h / 20 °C 8.1: 91 percent / NaBH3CN / acetonitrile / 0.5 h / 20 °C View Scheme

1.1: 627 g / t-BuOK / dimethylsulfoxide / 3 h / 20 °C 2.1: 82 percent / 3-chloroperoxybenzoic acid; sodium bicarbonate / CH2Cl2 / 2 h / 20 °C 3.1: n-BuLi / 1,2-dimethoxy-ethane; hexane / 0.17 h / -78 °C 3.2: 45 percent / 1,2-dimethoxy-ethane; hexane / 1 h / -78 °C 4.1: 66 percent / Na-Hg; Na2HPO4 / methanol / 2.5 h / 20 °C 5.1: 100 percent / Jones reagent / acetone / 0.5 h / 20 °C 6.1: 100 percent / trifluoroacetic acid / CH2Cl2 / 1.5 h / 20 °C 7.1: 91 percent / NaBH3CN / acetonitrile / 0.5 h / 20 °C View Scheme

1: BF3*Et2O / CH2Cl2 / 12 h / -78 - 20 °C 2: 97 percent / Dess-Martin reagent / CH2Cl2 / 1 h / Ambient temperature 3: 91 percent / NaN(TMS)2 / diethyl ether / 1.5 h / 0 °C 4: 1.) BH3*THF; 2.) aq. 30 percent H2O2, aq. NaOH / 1.) THF, -78 deg C, 3 h; 2.) THF, 0 deg C, 0.5 h 5: Et3N, DMAP / CH2Cl2 / 3 h / 0 °C 6: t-BuOK / dimethylsulfoxide / 12 h / Ambient temperature 7: mCPBA, NaHCO3 / CH2Cl2 / 3.5 h / Ambient temperature View Scheme

Multistep reaction;