1: 1.) n-BuLi / 1.) THF, hexane, 0-5 deg C; 2.) -20 deg C, 2 h 2: n-Bu3SnH, AIBN / benzene / 12 h / Heating 3: Ph3P, diisopropyl azodicarboxylate / tetrahydrofuran / 20 h / Ambient temperature 4: DMAP / CH2Cl2 / 4 h / Ambient temperature 5: NaOCH3 / methanol / 0.67 h / 0 - 5 °C 6: 1.) n-BuLi / 1.) THF, hexane, 0-5 deg C; 2.) room temp., 13 h 7: 6 percent / n-Bu4NIO4, Na2HPO4 / CDCl3 / 1.75 h / Ambient temperature View Scheme

1.1: 98 percent / imidazole / dimethylformamide / 0.67 h / 20 °C 2.1: 81 percent Turnov. / LiOH*H2O / methanol / 48 h / -5 °C 3.1: diphenylphosphorazidate; Et3N / benzene / 1 h 3.2: toluene / 1 h / 110 °C 4.1: n-BuLi / tetrahydrofuran; pentane / 0.5 h / -100 °C 4.2: tetrahydrofuran; toluene; pentane / 0.75 h / -100 °C 5.1: NaH / dimethylformamide / 0.5 h / -5 °C 5.2: dimethylformamide / 0.25 h / -5 °C 6.1: 76 percent / pyridinium p-toluenesulfonate / methanol / 2 h / 20 °C 7.1: 30 percent / benzene / 48 h / 5 °C / UV-irradiation 8.1: NaBH4 / ethanol / 16 h / 20 °C 9.1: 12.9 mg / aq. H2O2 / tetrahydrofuran; ethanol / 22 h / 20 °C 10.1: NaH / tetrahydrofuran / 0.33 h / 20 °C 10.2: 94 percent / tetrahydrofuran / 20 h / 20 °C 11.1: pyridine; trimethylamine-N-oxide dihydrate; H2O / OsO4; acetone / 2-methyl-propan-2-ol; tetrahydrofuran / 15 h / 20 °C 12.1: 19.2 mg / p-TsOH / 2 h / 20 °C 13.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 0 °C 14.1: 7.1 mg / Burgess reagent / benzene / 16 h / Heating 15.1: 3.3 mg / K2CO3; H2O / methanol / 20 °C 16.1: n-BuLi; oxygen / tetrahydrofuran; hexane / 0.25 h / -78 °C 16.2: 45 percent / NH4Cl; H2O; dimethylsulfide / tetrahydrofuran; hexane / 1 h / 20 °C 17.1: 59 percent / H2O / p-toluenesulfonic acid / CHCl3; methanol / 0.5 h / 0 °C View Scheme

Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) THF, hexane, 0-5 deg C; 2.) -20 deg C, 2 h2: n-Bu3SnH, AIBN / benzene / 12 h / Heating  

Multi-step reaction with 3 steps 1: 1.) n-BuLi / 1.) THF, hexane, 0-5 deg C; 2.) -20 deg C, 2 h2: n-Bu3SnH, AIBN / benzene / 12 h / Heating3: Ph3P, diisopropyl azodicarboxylate / tetrahydrofuran / 20 h / Ambient temperature  

Multi-step reaction with 6 steps 1: 1.) n-BuLi / 1.) THF, hexane, 0-5 deg C; 2.) -20 deg C, 2 h2: n-Bu3SnH, AIBN / benzene / 12 h / Heating3: Ph3P, diisopropyl azodicarboxylate / tetrahydrofuran / 20 h / Ambient temperature4: DMAP / CH2Cl2 / 4 h / Ambient temperature5: NaOCH3 / methanol / 0.67 h / 0 - 5 °C6: 1.) n-BuLi / 1.) THF, hexane, 0-5 deg C; 2.) room temp., 13 h  

Multi-step reaction with 4 steps 1: 1.) n-BuLi / 1.) THF, hexane, 0-5 deg C; 2.) -20 deg C, 2 h2: n-Bu3SnH, AIBN / benzene / 12 h / Heating3: Ph3P, diisopropyl azodicarboxylate / tetrahydrofuran / 20 h / Ambient temperature4: DMAP / CH2Cl2 / 4 h / Ambient temperature  

Multi-step reaction with 5 steps 1: 1.) n-BuLi / 1.) THF, hexane, 0-5 deg C; 2.) -20 deg C, 2 h2: n-Bu3SnH, AIBN / benzene / 12 h / Heating3: Ph3P, diisopropyl azodicarboxylate / tetrahydrofuran / 20 h / Ambient temperature4: DMAP / CH2Cl2 / 4 h / Ambient temperature5: NaOCH3 / methanol / 0.67 h / 0 - 5 °C  

Multi-step reaction with 7 steps 1: 1.) n-BuLi / 1.) THF, hexane, 0-5 deg C; 2.) -20 deg C, 2 h2: n-Bu3SnH, AIBN / benzene / 12 h / Heating3: Ph3P, diisopropyl azodicarboxylate / tetrahydrofuran / 20 h / Ambient temperature4: DMAP / CH2Cl2 / 4 h / Ambient temperature5: NaOCH3 / methanol / 0.67 h / 0 - 5 °C6: 1.) n-BuLi / 1.) THF, hexane, 0-5 deg C; 2.) room temp., 13 h7: 75 percent / n-Bu4NIO4, Na2HPO4 / CDCl3 / 1.75 h / Ambient temperature