hydrogen; palladium dihydroxide in ethyl acetate T=20°C; 10 h;

boron trifluoride diethyl etherate in acetonitrile T=0°C; 2 h;

1.1: magnesium / diethyl ether 1.2: 98 percent / CuI / diethyl ether / 12 h / -78 - -20 °C 2.1: 96 percent / KOH / diethyl ether / 6 h / 0 - 20 °C 3.1: 95 percent / CuI / tetrahydrofuran / 12 h / -78 °C 4.1: NaH / dimethylformamide / 0.5 h / 20 °C 4.2: 97 percent / tetra-n-butylammonium iodide / dimethylformamide / 1 h / 0 °C 5.1: BH3*DMS / tetrahydrofuran / 4 h / 0 - 20 °C 5.2: 88 percent / NaOH; H2O2 / methanol; H2O / 6 h / 20 °C 6.1: DMSO; oxalyl chloride / CH2Cl2 / 1.5 h / -78 - -60 °C 6.2: Et3N / CH2Cl2 / 1 h / -60 °C 7.1: 3.27 g / acetone / 24 h / 20 °C 8.1: 96 percent / osmium tetroxide; methanesulfonamide; (DHQ)2PHAL / K2CO3; K3Fe(CN)6 / toluene; 2-methyl-propan-2-ol; H2O / 24 h / 0 °C 9.1: Et3N; SOCl2 / CH2Cl2 / 0.5 h / 0 °C 9.2: 98 percent / RuCl3*H2O; NaIO4 / acetonitrile; CCl4; H2O / 1 h / 20 °C 10.1: NaBH4; DMAC / 0.5 h / 25 °C 10.2: 86 percent / aq. H2SO4 / 20 °C 11.1: 81 percent / H2 / Pd(OH)2/C / ethyl acetate / 10 h / 20 °C View Scheme

1.1: DMSO; oxalyl chloride / CH2Cl2 / 1.5 h / -78 - -60 °C 1.2: Et3N / CH2Cl2 / 1 h / -60 °C 2.1: 3.27 g / acetone / 24 h / 20 °C 3.1: 96 percent / osmium tetroxide; methanesulfonamide; (DHQ)2PHAL / K2CO3; K3Fe(CN)6 / toluene; 2-methyl-propan-2-ol; H2O / 24 h / 0 °C 4.1: Et3N; SOCl2 / CH2Cl2 / 0.5 h / 0 °C 4.2: 98 percent / RuCl3*H2O; NaIO4 / acetonitrile; CCl4; H2O / 1 h / 20 °C 5.1: NaBH4; DMAC / 0.5 h / 25 °C 5.2: 86 percent / aq. H2SO4 / 20 °C 6.1: 81 percent / H2 / Pd(OH)2/C / ethyl acetate / 10 h / 20 °C View Scheme

1.1: 96 percent / osmium tetroxide; methanesulfonamide; (DHQ)2PHAL / K2CO3; K3Fe(CN)6 / toluene; 2-methyl-propan-2-ol; H2O / 24 h / 0 °C 2.1: Et3N; SOCl2 / CH2Cl2 / 0.5 h / 0 °C 2.2: 98 percent / RuCl3*H2O; NaIO4 / acetonitrile; CCl4; H2O / 1 h / 20 °C 3.1: NaBH4; DMAC / 0.5 h / 25 °C 3.2: 86 percent / aq. H2SO4 / 20 °C 4.1: 81 percent / H2 / Pd(OH)2/C / ethyl acetate / 10 h / 20 °C View Scheme

1.1: Et3N; SOCl2 / CH2Cl2 / 0.5 h / 0 °C 1.2: 98 percent / RuCl3*H2O; NaIO4 / acetonitrile; CCl4; H2O / 1 h / 20 °C 2.1: NaBH4; DMAC / 0.5 h / 25 °C 2.2: 86 percent / aq. H2SO4 / 20 °C 3.1: 81 percent / H2 / Pd(OH)2/C / ethyl acetate / 10 h / 20 °C View Scheme

1.1: NaBH4; DMAC / 0.5 h / 25 °C 1.2: 86 percent / aq. H2SO4 / 20 °C 2.1: 81 percent / H2 / Pd(OH)2/C / ethyl acetate / 10 h / 20 °C View Scheme

1.1: BH3*SMe2 / tetrahydrofuran / 2.5 h / -78 - 0 °C 1.2: 85 percent / NaOH; H2O2 / H2O / 3.5 h / 20 °C 2.1: 95 percent / Dess-Martin reagent / CH2Cl2 / 2 h / 20 °C 3.1: diethyl ether / 5 h / -100 - 23 °C 3.2: NaOH; H2O2 / H2O / 1 h / Heating 4.1: 98 percent / imidazole / dimethylformamide / 24 h / 30 °C 5.1: O3 / CH2Cl2 / -78 °C 5.2: 90 percent / PPh3 / 4 h / 20 °C 6.1: 90 percent / NaH2PO4; KMnO4 / H2O; 2-methyl-propan-2-ol / 0.5 h / 20 °C 7.1: 93 percent / BF3*Et2O / acetonitrile / 2 h / 0 °C View Scheme

1.1: diethyl ether / 5 h / -100 - 23 °C 1.2: NaOH; H2O2 / H2O / 1 h / Heating 2.1: 98 percent / imidazole / dimethylformamide / 24 h / 30 °C 3.1: O3 / CH2Cl2 / -78 °C 3.2: 90 percent / PPh3 / 4 h / 20 °C 4.1: 90 percent / NaH2PO4; KMnO4 / H2O; 2-methyl-propan-2-ol / 0.5 h / 20 °C 5.1: 93 percent / BF3*Et2O / acetonitrile / 2 h / 0 °C View Scheme

1.1: 95 percent / Dess-Martin reagent / CH2Cl2 / 2 h / 20 °C 2.1: diethyl ether / 5 h / -100 - 23 °C 2.2: NaOH; H2O2 / H2O / 1 h / Heating 3.1: 98 percent / imidazole / dimethylformamide / 24 h / 30 °C 4.1: O3 / CH2Cl2 / -78 °C 4.2: 90 percent / PPh3 / 4 h / 20 °C 5.1: 90 percent / NaH2PO4; KMnO4 / H2O; 2-methyl-propan-2-ol / 0.5 h / 20 °C 6.1: 93 percent / BF3*Et2O / acetonitrile / 2 h / 0 °C View Scheme