1: anhydrous potassium carbonate / butan-2-one / 24 h / Heating 2: 89 percent / N,N,N',N'-tetramethylethylenediamine / 12 h / 200 °C 3: 100 percent / camphorsulfonic acid (CSA) / benzene / 12 h / Heating 4: 1.) sec-BuLi / 1.) THF, -78 deg C 5: 35 percent / NaH / dimethylsulfoxide / 24 h / 22 °C 6: H2 / 10percent Pd/C / dioxane / 0.75 h / 22 °C / 760 Torr 7: camphorsulfonic acid (CSA) / CH2Cl2; tetrahydrofuran / 5 h / 0 °C 8: 1.) LDA / 1.) THF, hexane, -78 deg C, 15 min, 2.) a) 30 min, b) 0 deg C, 1 h 9: 58 percent / camphorsulfonic acid (CSA) / methanol; benzene / 0.33 h / Heating View Scheme

1.1: triethylamine; magnesium chloride / acetonitrile / 55 - 68 °C 1.2: |Heating 2.1: N-bromosuccinmide / N,N-dimethyl-formamide / 4 h / 5 - 20 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 14 h / |Reflux View Scheme

1.1: tetrabutyl-ammonium chloride; hydrogenchloride / water; acetonitrile / |Electrochemical reaction 2.1: |Electrochemical reaction 3.1: |Electrochemical reaction 4.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 0 °C 5.1: 5 palladium on charcoal; hydrogen / methanol / 24 h / 20 °C 6.1: sodium hydroxide / methanol; water / 17 h / 0 °C 7.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / acetonitrile / 16 h / 20 °C 8.1: trichlorophosphate / toluene / 16 h / |Reflux 8.2: 6 h / -78 °C 9.1: hydrogen; palladium(II) oxide hydrate / ethyl acetate; methanol; water / 23 h / 20 °C 10.1: ammonia; sodium / 1,4-dioxane / 2 h / -78 °C View Scheme

1: K2CO3 / acetonitrile / 7 h / 80 °C 2: 1N aq. NaOH / methanol / 5 h / Ambient temperature View Scheme

1: 90 percent / NaBH4 / H2O / 8 h / Ambient temperature 2: 73 percent / 1N aq. NaOH / tetrahydrofuran / 1 h / Ambient temperature View Scheme

[bis(acetoxy)iodo]benzene in water; acetonitrile T=0°C;

1: 76 percent / potassium carbonate / acetone / 72 h / Heating 2: 82 percent / aq. KOH / ethanol / 18 h / Heating 3: 99 percent / oxalyl chloride, DMF / CH2Cl2 / 18 h View Scheme

1: 93 percent / NaOH / dimethylformamide / 4 h / 20 °C 2: 65 percent / NaOH / methanol / 4 h / Heating View Scheme

1: potassium carbonate / N,N-dimethyl-formamide; ethyl acetate 2: methanol; water View Scheme

1.1: tetrabutyl-ammonium chloride; hydrogenchloride / water; acetonitrile / |Electrochemical reaction 2.1: |Electrochemical reaction 3.1: |Electrochemical reaction 4.1: potassium carbonate / N,N-dimethyl-formamide / 7 h / 0 °C 5.1: 5 palladium on charcoal; hydrogen / methanol / 24 h / 20 °C 6.1: sodium hydroxide / methanol; water / 17 h / 0 °C 7.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / acetonitrile / 16 h / 20 °C 8.1: trichlorophosphate / toluene / 16 h / |Reflux 8.2: 6 h / -78 °C 9.1: hydrogen; palladium(II) oxide hydrate / ethyl acetate; methanol; water / 23 h / 20 °C 10.1: ammonia; sodium / 1,4-dioxane / 2 h / -78 °C View Scheme