1: 98 percent / BF3*Et2O / CH2Cl2 / 2 h / -20 - 20 °C 2: 94 percent / NaHCO3, m-CPBA / CH2Cl2 / 2 h / Ambient temperature 3: 1) n-BuLi / 1) DME, hexane, -50 deg C, 30 min, 2) DME, hexane, -60 deg C, 2 h 4: 68 percent / sodium amalgam, disodium hydrogen phosphate / methanol / 3 h / Ambient temperature 5: 95 percent / Jones reagent / acetone / 0.5 h / Ambient temperature 6: 92 percent / TFA / CH2Cl2 / 0.5 h / Ambient temperature 7: 70 percent / NaBH3CN, AcOH / acetonitrile; H2O / 1.33 h / pH 7 View Scheme

1: 96 percent / i-Bu2AlH / diethyl ether; hexane / 0.5 h 2: 98 percent / BF3*Et2O / CH2Cl2 / 2 h / -20 - 20 °C 3: 94 percent / NaHCO3, m-CPBA / CH2Cl2 / 2 h / Ambient temperature 4: 1) n-BuLi / 1) DME, hexane, -50 deg C, 30 min, 2) DME, hexane, -60 deg C, 2 h 5: 68 percent / sodium amalgam, disodium hydrogen phosphate / methanol / 3 h / Ambient temperature 6: 95 percent / Jones reagent / acetone / 0.5 h / Ambient temperature 7: 92 percent / TFA / CH2Cl2 / 0.5 h / Ambient temperature 8: 70 percent / NaBH3CN, AcOH / acetonitrile; H2O / 1.33 h / pH 7 View Scheme

1: 94 percent / t-BuOK / dimethylsulfoxide / 1 h / Ambient temperature 2: 96 percent / i-Bu2AlH / diethyl ether; hexane / 0.5 h 3: 98 percent / BF3*Et2O / CH2Cl2 / 2 h / -20 - 20 °C 4: 94 percent / NaHCO3, m-CPBA / CH2Cl2 / 2 h / Ambient temperature 5: 1) n-BuLi / 1) DME, hexane, -50 deg C, 30 min, 2) DME, hexane, -60 deg C, 2 h 6: 68 percent / sodium amalgam, disodium hydrogen phosphate / methanol / 3 h / Ambient temperature 7: 95 percent / Jones reagent / acetone / 0.5 h / Ambient temperature 8: 92 percent / TFA / CH2Cl2 / 0.5 h / Ambient temperature 9: 70 percent / NaBH3CN, AcOH / acetonitrile; H2O / 1.33 h / pH 7 View Scheme

1: NaOH / tetrahydrofuran; H2O / Ambient temperature 2: 96 percent / imidazole / dimethylformamide / Ambient temperature 3: 1) TMEDA, s-BuLi / 1) Et2O, cyclohexane, -78 deg C, 6 h, 2) Et2O, cyclohexane, -78 deg C -> room temperature, overnight 4: 93 percent / n-Bu4NF / tetrahydrofuran / 0 deg C, 1 h; room temperature, 2 h 5: 86 percent / N-methylmorpholine N-oxide, 4 Angstroem molecular sieves, (n-Pr)4NRuO4 / CH2Cl2 / Ambient temperature 6: 1) n-BuLi / 1) DME, hexane, -50 deg C, 30 min, 2) DME, hexane, -60 deg C, 2 h 7: 68 percent / sodium amalgam, disodium hydrogen phosphate / methanol / 3 h / Ambient temperature 8: 95 percent / Jones reagent / acetone / 0.5 h / Ambient temperature 9: 92 percent / TFA / CH2Cl2 / 0.5 h / Ambient temperature 10: 70 percent / NaBH3CN, AcOH / acetonitrile; H2O / 1.33 h / pH 7 View Scheme

1: 1) BF3*Et2O, BH3*Me2S, 2) aq. NaOH / 1) THF, reflux, 21 h, 2) THF, reflux, 4 h 2: NaOH / tetrahydrofuran; H2O / Ambient temperature 3: 96 percent / imidazole / dimethylformamide / Ambient temperature 4: 1) TMEDA, s-BuLi / 1) Et2O, cyclohexane, -78 deg C, 6 h, 2) Et2O, cyclohexane, -78 deg C -> room temperature, overnight 5: 93 percent / n-Bu4NF / tetrahydrofuran / 0 deg C, 1 h; room temperature, 2 h 6: 86 percent / N-methylmorpholine N-oxide, 4 Angstroem molecular sieves, (n-Pr)4NRuO4 / CH2Cl2 / Ambient temperature 7: 1) n-BuLi / 1) DME, hexane, -50 deg C, 30 min, 2) DME, hexane, -60 deg C, 2 h 8: 68 percent / sodium amalgam, disodium hydrogen phosphate / methanol / 3 h / Ambient temperature 9: 95 percent / Jones reagent / acetone / 0.5 h / Ambient temperature 10: 92 percent / TFA / CH2Cl2 / 0.5 h / Ambient temperature 11: 70 percent / NaBH3CN, AcOH / acetonitrile; H2O / 1.33 h / pH 7 View Scheme

1.1: ZnBr2 / tetrahydrofuran 1.2: 60 percent / ZnCl2; H2O 2.1: 50 percent / Huenig's base; lithium chloride / acetonitrile 3.1: trifluoroacetic acid / CH2Cl2 / 0 - 20 °C 3.2: sodium cyanoborohydride / CH2Cl2 4.1: TEA / CH2Cl2 5.1: H2 / PtO2 / ethanol 6.1: trifluoroacetic acid / CH2Cl2 7.1: NaBH3CN / acetonitrile View Scheme

1.1: L-tartaric acid 2.1: Et3N / tetrahydrofuran 3.1: 39 percent / NaIO4 / RuO4 / H2O; ethyl acetate 4.1: 54 percent / BuLi / tetrahydrofuran / -78 - 0 °C 5.1: 50 percent / Huenig's base; lithium chloride / acetonitrile 6.1: trifluoroacetic acid / CH2Cl2 / 0 - 20 °C 6.2: sodium cyanoborohydride / CH2Cl2 7.1: TEA / CH2Cl2 8.1: H2 / PtO2 / ethanol 9.1: trifluoroacetic acid / CH2Cl2 10.1: NaBH3CN / acetonitrile View Scheme

1.1: lithium perchlorate / diethyl ether / 168 h / 20 °C 2.1: 96 percent / H2 / 10 percent Pd/C / ethanol / 12 h / 20 °C / 760 Torr 3.1: 92 percent / LiN(TMS)2 / tetrahydrofuran / -78 - -40 °C 4.1: 83 percent / DBU / toluene / 5 h / 100 °C 5.1: 96 percent / H2 / PtO2 / ethanol / 16 h / 20 °C / 760 Torr 6.1: DIBAL-H / diethyl ether; hexane / 1 h / -78 °C 7.1: 1.50 g / BF3*Et2O / CH2Cl2 / 12 h / -60 °C 8.1: 95 percent / tetrapropylammonium perruthenate(VII); 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 9.1: NaN(TMS)2 / diethyl ether; toluene / 1 h / 20 °C 9.2: 86 percent / diethyl ether; toluene / 2 h / 20 °C 10.1: BH3*THF / tetrahydrofuran / 3 h / -78 °C 10.2: 73 percent / aq. NaOH; H2O2 / 0.5 h / 0 °C 11.1: triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 3 h / 0 °C 12.1: 627 g / t-BuOK / dimethylsulfoxide / 3 h / 20 °C 13.1: 82 percent / 3-chloroperoxybenzoic acid; sodium bicarbonate / CH2Cl2 / 2 h / 20 °C 14.1: n-BuLi / 1,2-dimethoxy-ethane; hexane / 0.17 h / -78 °C 14.2: 45 percent / 1,2-dimethoxy-ethane; hexane / 1 h / -78 °C 15.1: 66 percent / Na-Hg; Na2HPO4 / methanol / 2.5 h / 20 °C 16.1: 100 percent / Jones reagent / acetone / 0.5 h / 20 °C 17.1: 100 percent / trifluoroacetic acid / CH2Cl2 / 1.5 h / 20 °C 18.1: 91 percent / NaBH3CN / acetonitrile / 0.5 h / 20 °C View Scheme

1.1: lithium perchlorate / diethyl ether / 168 h / 20 °C 2.1: 96 percent / H2 / 10 percent Pd/C / ethanol / 12 h / 20 °C / 760 Torr 3.1: 92 percent / LiN(TMS)2 / tetrahydrofuran / -78 - -40 °C 4.1: 83 percent / DBU / toluene / 5 h / 100 °C 5.1: 96 percent / H2 / PtO2 / ethanol / 16 h / 20 °C / 760 Torr 6.1: DIBAL-H / diethyl ether; hexane / 1 h / -78 °C 7.1: 1.50 g / BF3*Et2O / CH2Cl2 / 12 h / -60 °C 8.1: 95 percent / tetrapropylammonium perruthenate(VII); 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 9.1: NaN(TMS)2 / diethyl ether; toluene / 1 h / 20 °C 9.2: 86 percent / diethyl ether; toluene / 2 h / 20 °C 10.1: BH3*THF / tetrahydrofuran / 3 h / -78 °C 10.2: 73 percent / aq. NaOH; H2O2 / 0.5 h / 0 °C 11.1: triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 3 h / 0 °C 12.1: 627 g / t-BuOK / dimethylsulfoxide / 3 h / 20 °C 13.1: 82 percent / 3-chloroperoxybenzoic acid; sodium bicarbonate / CH2Cl2 / 2 h / 20 °C 14.1: n-BuLi / 1,2-dimethoxy-ethane; hexane / 0.17 h / -78 °C 14.2: 45 percent / 1,2-dimethoxy-ethane; hexane / 1 h / -78 °C 15.1: 66 percent / Na-Hg; Na2HPO4 / methanol / 2.5 h / 20 °C 16.1: 100 percent / Jones reagent / acetone / 0.5 h / 20 °C 17.1: 100 percent / trifluoroacetic acid / CH2Cl2 / 1.5 h / 20 °C 18.1: 91 percent / NaBH3CN / acetonitrile / 0.5 h / 20 °C View Scheme

1.1: 92 percent / LiN(TMS)2 / tetrahydrofuran / -78 - -40 °C 2.1: 83 percent / DBU / toluene / 5 h / 100 °C 3.1: 96 percent / H2 / PtO2 / ethanol / 16 h / 20 °C / 760 Torr 4.1: DIBAL-H / diethyl ether; hexane / 1 h / -78 °C 5.1: 1.50 g / BF3*Et2O / CH2Cl2 / 12 h / -60 °C 6.1: 95 percent / tetrapropylammonium perruthenate(VII); 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C 7.1: NaN(TMS)2 / diethyl ether; toluene / 1 h / 20 °C 7.2: 86 percent / diethyl ether; toluene / 2 h / 20 °C 8.1: BH3*THF / tetrahydrofuran / 3 h / -78 °C 8.2: 73 percent / aq. NaOH; H2O2 / 0.5 h / 0 °C 9.1: triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 3 h / 0 °C 10.1: 627 g / t-BuOK / dimethylsulfoxide / 3 h / 20 °C 11.1: 82 percent / 3-chloroperoxybenzoic acid; sodium bicarbonate / CH2Cl2 / 2 h / 20 °C 12.1: n-BuLi / 1,2-dimethoxy-ethane; hexane / 0.17 h / -78 °C 12.2: 45 percent / 1,2-dimethoxy-ethane; hexane / 1 h / -78 °C 13.1: 66 percent / Na-Hg; Na2HPO4 / methanol / 2.5 h / 20 °C 14.1: 100 percent / Jones reagent / acetone / 0.5 h / 20 °C 15.1: 100 percent / trifluoroacetic acid / CH2Cl2 / 1.5 h / 20 °C 16.1: 91 percent / NaBH3CN / acetonitrile / 0.5 h / 20 °C View Scheme