1: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h 2: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating 3: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 4: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 5: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 6: tetrahydrofuran / 20 h / 23 °C 7: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 8: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 9: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 10: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 11: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme

Multi-step reaction with 7 steps 1: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h2: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating3: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min4: 83 percent / acetyl chloride / methanol / 2 h / 50 °C5: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C6: tetrahydrofuran / 20 h / 23 °C7: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C  

Multi-step reaction with 8 steps 1: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h2: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating3: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min4: 83 percent / acetyl chloride / methanol / 2 h / 50 °C5: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C6: tetrahydrofuran / 20 h / 23 °C7: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C8: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C  

Multi-step reaction with 9 steps 1: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h2: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating3: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min4: 83 percent / acetyl chloride / methanol / 2 h / 50 °C5: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C6: tetrahydrofuran / 20 h / 23 °C7: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C8: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C9: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C  

Multi-step reaction with 5 steps 1: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h2: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating3: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min4: 83 percent / acetyl chloride / methanol / 2 h / 50 °C5: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C  

With  N-bromosuccinmide; sulfuric acid in  tetrahydrofuran T=-23°C; 1 h;   

Multi-step reaction with 8 steps 1: 92 percent / K2CO3 / 4-(dimethylamino)pyridine / tetrahydrofuran / 4 h / 23 °C2: 94 percent / K2CO3 / n-Bu4NI / acetone / 16 h / Heating3: 90 percent / Na2S2O4 / tetrahydrofuran; H2O / 30 h / Heating4: pyridine / tetrahydrofuran / 18 h / 22 °C5: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C6: CH2Cl2 / 10 h / 23 °C7: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C8: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C  

Multi-step reaction with 5 steps 1: pyridine / tetrahydrofuran / 18 h / 22 °C2: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C3: CH2Cl2 / 10 h / 23 °C4: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C5: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C  

Multi-step reaction with 6 steps 1: 90 percent / Na2S2O4 / tetrahydrofuran; H2O / 30 h / Heating2: pyridine / tetrahydrofuran / 18 h / 22 °C3: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C4: CH2Cl2 / 10 h / 23 °C5: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C6: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C  

Multi-step reaction with 3 steps 1: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h2: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating3: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min