hydrogenchloride; lithium hydroxide; ammonium hydroxide in methanol; water

1: pTsOH*H2O / 20 °C 2: 64 percent / BF3*Et2O / CH2Cl2 / 3 h / -78 - -50 °C 3: 70 percent / aq. HCl; AcOH / 3 h / 20 °C View Scheme

1: lithium triethylborohydride / tetrahydrofuran / 0.5 h / -78 °C 2: pTsOH*H2O / 20 °C 3: 64 percent / BF3*Et2O / CH2Cl2 / 3 h / -78 - -50 °C 4: 70 percent / aq. HCl; AcOH / 3 h / 20 °C View Scheme

1: 64 percent / BF3*Et2O / CH2Cl2 / 3 h / -78 - -50 °C 2: 70 percent / aq. HCl; AcOH / 3 h / 20 °C View Scheme

1.1: (-)-dimethyl D-tartrate; titanium tetraisopropoxide; tert-butylhydroperoxide / molecular sieves 4 Angstroem / CH2Cl2; decane / 4 h / -20 °C 2.1: 7.35 g / trimethylphosphite; triethylamine / CH2Cl2; decane / 1.5 h 3.1: 63 percent / lithium aluminum hydride / tetrahydrofuran / 0 - 20 °C 4.1: 98 percent / sodium hydride / tetrahydrofuran / 16 h / 0 - 20 °C 5.1: 98 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 16 h / 0 - 20 °C 6.1: hydrogen / 20percent Pd(OH)2 on carbon / CH2Cl2 / 3.5 h 7.1: 1.74 g / pyridinium chlorochromate; molecular sieves 4 Angstroem; Celite / CH2Cl2 / 1.5 h / 20 °C 8.1: pyridinium p-toluenesulfonate; MgSO4 / diethyl ether / 18 h / 20 °C 9.1: 52 percent / BF3*Et2O / diethyl ether / 3 h / -78 - -50 °C 10.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 3 h / Heating 10.2: CuBr*Me2S; trimethylsilylchloride / tetrahydrofuran / 1.67 h / -78 °C 10.3: 6.9 g / tetrahydrofuran / 1 h / -78 °C 11.1: diisobutylaluminum hydride / hexane; tetrahydrofuran / 0.75 h / -78 °C 12.1: pyridinium p-toluenesulfonate / 1 h / 20 °C 13.1: 4.4 g / BF3*Et2O / CH2Cl2 / 0.5 h / -78 °C 14.1: methanol; pyridinium p-toluenesulfonate / 18 h / Heating 15.1: 1.92 g / triethylamine / CH2Cl2 / 1 h / 20 °C 16.1: hydrochloric acid / 42 h / 60 °C View Scheme

1.1: 80 percent / lithium aluminum hydride / diethyl ether / 2 h / 0 - 20 °C 2.1: (-)-dimethyl D-tartrate; titanium tetraisopropoxide; tert-butylhydroperoxide / molecular sieves 4 Angstroem / CH2Cl2; decane / 4 h / -20 °C 3.1: 7.35 g / trimethylphosphite; triethylamine / CH2Cl2; decane / 1.5 h 4.1: 63 percent / lithium aluminum hydride / tetrahydrofuran / 0 - 20 °C 5.1: 98 percent / sodium hydride / tetrahydrofuran / 16 h / 0 - 20 °C 6.1: 98 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 16 h / 0 - 20 °C 7.1: hydrogen / 20percent Pd(OH)2 on carbon / CH2Cl2 / 3.5 h 8.1: 1.74 g / pyridinium chlorochromate; molecular sieves 4 Angstroem; Celite / CH2Cl2 / 1.5 h / 20 °C 9.1: pyridinium p-toluenesulfonate; MgSO4 / diethyl ether / 18 h / 20 °C 10.1: 52 percent / BF3*Et2O / diethyl ether / 3 h / -78 - -50 °C 11.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 3 h / Heating 11.2: CuBr*Me2S; trimethylsilylchloride / tetrahydrofuran / 1.67 h / -78 °C 11.3: 6.9 g / tetrahydrofuran / 1 h / -78 °C 12.1: diisobutylaluminum hydride / hexane; tetrahydrofuran / 0.75 h / -78 °C 13.1: pyridinium p-toluenesulfonate / 1 h / 20 °C 14.1: 4.4 g / BF3*Et2O / CH2Cl2 / 0.5 h / -78 °C 15.1: methanol; pyridinium p-toluenesulfonate / 18 h / Heating 16.1: 1.92 g / triethylamine / CH2Cl2 / 1 h / 20 °C 17.1: hydrochloric acid / 42 h / 60 °C View Scheme

1.1: 98 percent / sodium hydride / tetrahydrofuran / 16 h / 0 - 20 °C 2.1: 98 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 16 h / 0 - 20 °C 3.1: hydrogen / 20percent Pd(OH)2 on carbon / CH2Cl2 / 3.5 h 4.1: 1.74 g / pyridinium chlorochromate; molecular sieves 4 Angstroem; Celite / CH2Cl2 / 1.5 h / 20 °C 5.1: pyridinium p-toluenesulfonate; MgSO4 / diethyl ether / 18 h / 20 °C 6.1: 52 percent / BF3*Et2O / diethyl ether / 3 h / -78 - -50 °C 7.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 3 h / Heating 7.2: CuBr*Me2S; trimethylsilylchloride / tetrahydrofuran / 1.67 h / -78 °C 7.3: 6.9 g / tetrahydrofuran / 1 h / -78 °C 8.1: diisobutylaluminum hydride / hexane; tetrahydrofuran / 0.75 h / -78 °C 9.1: pyridinium p-toluenesulfonate / 1 h / 20 °C 10.1: 4.4 g / BF3*Et2O / CH2Cl2 / 0.5 h / -78 °C 11.1: methanol; pyridinium p-toluenesulfonate / 18 h / Heating 12.1: 1.92 g / triethylamine / CH2Cl2 / 1 h / 20 °C 13.1: hydrochloric acid / 42 h / 60 °C View Scheme

1.1: 63 percent / lithium aluminum hydride / tetrahydrofuran / 0 - 20 °C 2.1: 98 percent / sodium hydride / tetrahydrofuran / 16 h / 0 - 20 °C 3.1: 98 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 16 h / 0 - 20 °C 4.1: hydrogen / 20percent Pd(OH)2 on carbon / CH2Cl2 / 3.5 h 5.1: 1.74 g / pyridinium chlorochromate; molecular sieves 4 Angstroem; Celite / CH2Cl2 / 1.5 h / 20 °C 6.1: pyridinium p-toluenesulfonate; MgSO4 / diethyl ether / 18 h / 20 °C 7.1: 52 percent / BF3*Et2O / diethyl ether / 3 h / -78 - -50 °C 8.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 3 h / Heating 8.2: CuBr*Me2S; trimethylsilylchloride / tetrahydrofuran / 1.67 h / -78 °C 8.3: 6.9 g / tetrahydrofuran / 1 h / -78 °C 9.1: diisobutylaluminum hydride / hexane; tetrahydrofuran / 0.75 h / -78 °C 10.1: pyridinium p-toluenesulfonate / 1 h / 20 °C 11.1: 4.4 g / BF3*Et2O / CH2Cl2 / 0.5 h / -78 °C 12.1: methanol; pyridinium p-toluenesulfonate / 18 h / Heating 13.1: 1.92 g / triethylamine / CH2Cl2 / 1 h / 20 °C 14.1: hydrochloric acid / 42 h / 60 °C View Scheme

1.1: 98 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 16 h / 0 - 20 °C 2.1: hydrogen / 20percent Pd(OH)2 on carbon / CH2Cl2 / 3.5 h 3.1: 1.74 g / pyridinium chlorochromate; molecular sieves 4 Angstroem; Celite / CH2Cl2 / 1.5 h / 20 °C 4.1: pyridinium p-toluenesulfonate; MgSO4 / diethyl ether / 18 h / 20 °C 5.1: 52 percent / BF3*Et2O / diethyl ether / 3 h / -78 - -50 °C 6.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 3 h / Heating 6.2: CuBr*Me2S; trimethylsilylchloride / tetrahydrofuran / 1.67 h / -78 °C 6.3: 6.9 g / tetrahydrofuran / 1 h / -78 °C 7.1: diisobutylaluminum hydride / hexane; tetrahydrofuran / 0.75 h / -78 °C 8.1: pyridinium p-toluenesulfonate / 1 h / 20 °C 9.1: 4.4 g / BF3*Et2O / CH2Cl2 / 0.5 h / -78 °C 10.1: methanol; pyridinium p-toluenesulfonate / 18 h / Heating 11.1: 1.92 g / triethylamine / CH2Cl2 / 1 h / 20 °C 12.1: hydrochloric acid / 42 h / 60 °C View Scheme

1.1: hydrogen / 20percent Pd(OH)2 on carbon / CH2Cl2 / 3.5 h 2.1: 1.74 g / pyridinium chlorochromate; molecular sieves 4 Angstroem; Celite / CH2Cl2 / 1.5 h / 20 °C 3.1: pyridinium p-toluenesulfonate; MgSO4 / diethyl ether / 18 h / 20 °C 4.1: 52 percent / BF3*Et2O / diethyl ether / 3 h / -78 - -50 °C 5.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 3 h / Heating 5.2: CuBr*Me2S; trimethylsilylchloride / tetrahydrofuran / 1.67 h / -78 °C 5.3: 6.9 g / tetrahydrofuran / 1 h / -78 °C 6.1: diisobutylaluminum hydride / hexane; tetrahydrofuran / 0.75 h / -78 °C 7.1: pyridinium p-toluenesulfonate / 1 h / 20 °C 8.1: 4.4 g / BF3*Et2O / CH2Cl2 / 0.5 h / -78 °C 9.1: methanol; pyridinium p-toluenesulfonate / 18 h / Heating 10.1: 1.92 g / triethylamine / CH2Cl2 / 1 h / 20 °C 11.1: hydrochloric acid / 42 h / 60 °C View Scheme