1: 65 percent / p-toluenesulfonic acid / tetrahydrofuran / 24 h / Heating 2: 1.) LDA / 1.) THF, from 0 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) 0 deg C, 1 h 3: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 0.33 h / 2068.6 Torr / Ambient temperature 4: 8 percent / triflic acid / tetrahydrofuran / 14 h / 0 °C 5: 92 percent / LiAlH4 / diethyl ether / 0.17 h / Ambient temperature 6: 1.) NaH, 2.) n-Bu4NI / 1.) THF, 2.) THF, reflux, 22 h 7: 96 percent / 1M aq. HCl / acetone / 4 h / Ambient temperature 8: 1.) CeCl3 / 1.) THF, -78 deg C, 1 h, 2.) THF, 10 min 9: 100 percent / H2 / 10percent Pd/C / ethanol / 0.17 h / 1034.3 Torr / Ambient temperature 10: 76 percent / p-TsOH / nitromethane / 0.5 h / 80 °C View Scheme

1: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 0.33 h / 2068.6 Torr / Ambient temperature 2: 8 percent / triflic acid / tetrahydrofuran / 14 h / 0 °C 3: 92 percent / LiAlH4 / diethyl ether / 0.17 h / Ambient temperature 4: 1.) NaH, 2.) n-Bu4NI / 1.) THF, 2.) THF, reflux, 22 h 5: 96 percent / 1M aq. HCl / acetone / 4 h / Ambient temperature 6: 1.) CeCl3 / 1.) THF, -78 deg C, 1 h, 2.) THF, 10 min 7: 100 percent / H2 / 10percent Pd/C / ethanol / 0.17 h / 1034.3 Torr / Ambient temperature 8: 76 percent / p-TsOH / nitromethane / 0.5 h / 80 °C View Scheme

1: 8 percent / triflic acid / tetrahydrofuran / 14 h / 0 °C 2: 92 percent / LiAlH4 / diethyl ether / 0.17 h / Ambient temperature 3: 1.) NaH, 2.) n-Bu4NI / 1.) THF, 2.) THF, reflux, 22 h 4: 96 percent / 1M aq. HCl / acetone / 4 h / Ambient temperature 5: 1.) CeCl3 / 1.) THF, -78 deg C, 1 h, 2.) THF, 10 min 6: 100 percent / H2 / 10percent Pd/C / ethanol / 0.17 h / 1034.3 Torr / Ambient temperature 7: 76 percent / p-TsOH / nitromethane / 0.5 h / 80 °C View Scheme

1: 1.) LDA / 1.) THF, from 0 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) 0 deg C, 1 h 2: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 0.33 h / 2068.6 Torr / Ambient temperature 3: 8 percent / triflic acid / tetrahydrofuran / 14 h / 0 °C 4: 92 percent / LiAlH4 / diethyl ether / 0.17 h / Ambient temperature 5: 1.) NaH, 2.) n-Bu4NI / 1.) THF, 2.) THF, reflux, 22 h 6: 96 percent / 1M aq. HCl / acetone / 4 h / Ambient temperature 7: 1.) CeCl3 / 1.) THF, -78 deg C, 1 h, 2.) THF, 10 min 8: 100 percent / H2 / 10percent Pd/C / ethanol / 0.17 h / 1034.3 Torr / Ambient temperature 9: 76 percent / p-TsOH / nitromethane / 0.5 h / 80 °C View Scheme

1: 13 percent / p-toluenesulfonic acid / tetrahydrofuran / 24 h / Heating 2: 65 percent / p-toluenesulfonic acid / tetrahydrofuran / 24 h / Heating 3: 1.) LDA / 1.) THF, from 0 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) 0 deg C, 1 h 4: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 0.33 h / 2068.6 Torr / Ambient temperature 5: 8 percent / triflic acid / tetrahydrofuran / 14 h / 0 °C 6: 92 percent / LiAlH4 / diethyl ether / 0.17 h / Ambient temperature 7: 1.) NaH, 2.) n-Bu4NI / 1.) THF, 2.) THF, reflux, 22 h 8: 96 percent / 1M aq. HCl / acetone / 4 h / Ambient temperature 9: 1.) CeCl3 / 1.) THF, -78 deg C, 1 h, 2.) THF, 10 min 10: 100 percent / H2 / 10percent Pd/C / ethanol / 0.17 h / 1034.3 Torr / Ambient temperature 11: 76 percent / p-TsOH / nitromethane / 0.5 h / 80 °C View Scheme

1: 25 percent / p-toluenesulfonic acid / tetrahydrofuran / 24 h / Heating 2: 65 percent / p-toluenesulfonic acid / tetrahydrofuran / 24 h / Heating 3: 1.) LDA / 1.) THF, from 0 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) 0 deg C, 1 h 4: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 0.33 h / 2068.6 Torr / Ambient temperature 5: 8 percent / triflic acid / tetrahydrofuran / 14 h / 0 °C 6: 92 percent / LiAlH4 / diethyl ether / 0.17 h / Ambient temperature 7: 1.) NaH, 2.) n-Bu4NI / 1.) THF, 2.) THF, reflux, 22 h 8: 96 percent / 1M aq. HCl / acetone / 4 h / Ambient temperature 9: 1.) CeCl3 / 1.) THF, -78 deg C, 1 h, 2.) THF, 10 min 10: 100 percent / H2 / 10percent Pd/C / ethanol / 0.17 h / 1034.3 Torr / Ambient temperature 11: 76 percent / p-TsOH / nitromethane / 0.5 h / 80 °C View Scheme

methanesulfonic acid in dichloromethane T=20°C; 0.25 - 2 h; Product distribution / selectivity;

1: O3; pyridine / CH2Cl2 / -78 °C 2: 72 mg / LiAlH4 / tetrahydrofuran / 0 - 20 °C 3: 87 percent / p-toluenesulfonic acid / nitromethane / 3 h / 20 °C View Scheme

1: 99 percent / conc. H2SO4 / dimethylsulfoxide / 1 h / Ambient temperature 2: 99 percent / p-dimethylaminopyridine, pyridine / 1 h / Ambient temperature 4: 96 percent / H2 / 20percent Pd(OH)2-C / methanol / Ambient temperature 5: 98 percent / conc. H2SO4 / dimethylsulfoxide / 0.5 h / Ambient temperature 6: 93 percent / LiAlH4, AlCl3 / diethyl ether / 0.5 h / -20 °C 7: 98 percent / CBr4, Ph3P / tetrahydrofuran / 0.25 h / Ambient temperature 8: 99 percent / H2 / 20percent Pd(OH)2-C / ethyl acetate / Ambient temperature 9: 97 percent / dimethylsulfoxide / 12 h / 40 °C 10: 96 percent / CrO3, H2SO4 / acetone / 0 °C 11: 89 percent / 6 M aq. NaOH / methanol / 1 h / Heating 12: tetrahydrofuran; diethyl ether / 1.) -70 deg C, 1 h, 2.) 0 deg C, 30 min 13: p-TsOH*H2O / toluene / 0.5 h / Heating 14: 76 percent / LiAlH4 / diethyl ether / 0.5 h / Ambient temperature 15: 45 percent / p-TsOH*H2O / nitromethane / 0.08 h / 40 °C View Scheme

1: 98 percent / conc. H2SO4 / dimethylsulfoxide / 0.5 h / Ambient temperature 2: 93 percent / LiAlH4, AlCl3 / diethyl ether / 0.5 h / -20 °C 3: 98 percent / CBr4, Ph3P / tetrahydrofuran / 0.25 h / Ambient temperature 4: 99 percent / H2 / 20percent Pd(OH)2-C / ethyl acetate / Ambient temperature 5: 97 percent / dimethylsulfoxide / 12 h / 40 °C 6: 96 percent / CrO3, H2SO4 / acetone / 0 °C 7: 89 percent / 6 M aq. NaOH / methanol / 1 h / Heating 8: tetrahydrofuran; diethyl ether / 1.) -70 deg C, 1 h, 2.) 0 deg C, 30 min 9: p-TsOH*H2O / toluene / 0.5 h / Heating 10: 76 percent / LiAlH4 / diethyl ether / 0.5 h / Ambient temperature 11: 45 percent / p-TsOH*H2O / nitromethane / 0.08 h / 40 °C View Scheme