1: 90 percent / pyridine / pyridine / 48 h / 23 °C 2: 96 percent / hydrogen / 5percent Pd/BaSO4 / pyridine / 6 h / 23 °C 3: 40 percent / ozone / CH2Cl2 / 3 h / -78 °C 4: 1.) Jones reagent, sodium hydroxide / 1.) acetone, 0 deg C, 15 min, 2.) methanol, RT, 1 h View Scheme

1: 71 percent / triethylamine / CH2Cl2 / 15 h / Ambient temperature 2: 1.) n-butyllithium, 2.) boron trifluoride etherate / 1.) THF, hexane, 2.) THF, hexane, -78 deg C 3: 40.1 percent / 4-(dimethylamino)pyridine, diisopropylethylamine / 8 h / 45 °C 4: 55.6 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating 5: 92 percent / 2.) 0.5 N aq. sulfuric acid / acetonitrile / 16 h / 23 °C 6: 1.) dimsylsodium, sodium carbonate / 1.) 23 deg C, 20 min, 2.) 23 deg C, 4 h View Scheme

Multi-step reaction with 8 steps 1: 82 percent / chromium trioxide, conc. sulfuric acid / acetone / 1 h / 0 °C2: 1.) (S)-Alpine Borane, 2.) sodium hydroxide, 30 percent hydrogen peroxide / 1.) THF, 23 deg C, 16 h, 2.) THF, 40 deg C, 3 h3: 71 percent / triethylamine / CH2Cl2 / 15 h / Ambient temperature4: 1.) n-butyllithium, 2.) boron trifluoride etherate / 1.) THF, hexane, 2.) THF, hexane, -78 deg C5: 35.1 percent / 4-(dimethylamino)pyridine, diisopropylethylamine / 8 h / 45 °C6: LiAlH4 / tetrahydrofuran / 1 h / Heating7: 2.) 0.5 N aq. sulfuric acid / acetonitrile / 16 h / 23 °C8: 1.) dimsylsodium, sodium carbonate / 1.) 23 deg C, 20 min, 2.) 23 deg C, 4 h  

Multi-step reaction with 3 steps 1: 82 percent / chromium trioxide, conc. sulfuric acid / acetone / 1 h / 0 °C2: 1.) (S)-Alpine Borane, 2.) sodium hydroxide, 30 percent hydrogen peroxide / 1.) THF, 23 deg C, 16 h, 2.) THF, 40 deg C, 3 h3: 71 percent / triethylamine / CH2Cl2 / 15 h / Ambient temperature  

Multi-step reaction with 7 steps 1: 82 percent / chromium trioxide, conc. sulfuric acid / acetone / 1 h / 0 °C2: 1.) (S)-Alpine Borane, 2.) sodium hydroxide, 30 percent hydrogen peroxide / 1.) THF, 23 deg C, 16 h, 2.) THF, 40 deg C, 3 h3: 71 percent / triethylamine / CH2Cl2 / 15 h / Ambient temperature4: 1.) n-butyllithium, 2.) boron trifluoride etherate / 1.) THF, hexane, 2.) THF, hexane, -78 deg C5: 40.1 percent / 4-(dimethylamino)pyridine, diisopropylethylamine / 8 h / 45 °C6: 55.6 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating7: 92 percent / 2.) 0.5 N aq. sulfuric acid / acetonitrile / 16 h / 23 °C  

With  methylmagnesium bromide; ammonium chloride in  tetrahydrofuran Show Experimental Procedure  

Multi-step reaction with 4 steps 1: 82 percent / chromium trioxide, conc. sulfuric acid / acetone / 1 h / 0 °C2: 1.) (S)-Alpine Borane, 2.) sodium hydroxide, 30 percent hydrogen peroxide / 1.) THF, 23 deg C, 16 h, 2.) THF, 40 deg C, 3 h3: 71 percent / triethylamine / CH2Cl2 / 15 h / Ambient temperature4: 1.) n-butyllithium, 2.) boron trifluoride etherate / 1.) THF, hexane, 2.) THF, hexane, -78 deg C  

Multi-step reaction with 8 steps 1: 82 percent / chromium trioxide, conc. sulfuric acid / acetone / 1 h / 0 °C2: 1.) (S)-Alpine Borane, 2.) sodium hydroxide, 30 percent hydrogen peroxide / 1.) THF, 23 deg C, 16 h, 2.) THF, 40 deg C, 3 h3: 71 percent / triethylamine / CH2Cl2 / 15 h / Ambient temperature4: 1.) n-butyllithium, 2.) boron trifluoride etherate / 1.) THF, hexane, 2.) THF, hexane, -78 deg C5: 40.1 percent / 4-(dimethylamino)pyridine, diisopropylethylamine / 8 h / 45 °C6: 55.6 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating7: 92 percent / 2.) 0.5 N aq. sulfuric acid / acetonitrile / 16 h / 23 °C8: 1.) dimsylsodium, sodium carbonate / 1.) 23 deg C, 20 min, 2.) 23 deg C, 4 h  

Multi-step reaction with 5 steps 1: 82 percent / chromium trioxide, conc. sulfuric acid / acetone / 1 h / 0 °C2: 1.) (S)-Alpine Borane, 2.) sodium hydroxide, 30 percent hydrogen peroxide / 1.) THF, 23 deg C, 16 h, 2.) THF, 40 deg C, 3 h3: 71 percent / triethylamine / CH2Cl2 / 15 h / Ambient temperature4: 1.) n-butyllithium, 2.) boron trifluoride etherate / 1.) THF, hexane, 2.) THF, hexane, -78 deg C5: 40.1 percent / 4-(dimethylamino)pyridine, diisopropylethylamine / 8 h / 45 °C  

Multi-step reaction with 5 steps 1: 82 percent / chromium trioxide, conc. sulfuric acid / acetone / 1 h / 0 °C2: 1.) (S)-Alpine Borane, 2.) sodium hydroxide, 30 percent hydrogen peroxide / 1.) THF, 23 deg C, 16 h, 2.) THF, 40 deg C, 3 h3: 90 percent / pyridine / pyridine / 48 h / 23 °C4: 96 percent / hydrogen / 5percent Pd/BaSO4 / pyridine / 6 h / 23 °C5: 40 percent / ozone / CH2Cl2 / 3 h / -78 °C