1.1: 75 percent / K2CO3 / acetone / 6 h / Heating 2.1: 76 percent / I2 / dimethylsulfoxide / 24 h / 110 °C 3.1: DMSO; 3 Angstroem molecular sieves / acetone; CH2Cl2 / -20 - 0 °C 3.2: 50 percent / TsOH*H2O / CH2Cl2 / 1 h / 20 °C 4.1: 85 percent / PPh3 / Pd2(dba)3*CHCl3 / CH2Cl2 / 3 h / 0 °C 5.1: 73 percent / NaBH4 / CH2Cl2; methanol / 3 h / -78 °C 6.1: 96 percent / OsO4; NMO / acetone; 2-methyl-propan-2-ol; H2O / 3 h / 0 °C 7.1: 86 percent / DMAP; pyridine / CH2Cl2 / 0 °C 8.1: 86 percent / H2 / Pd/C / tetrahydrofuran; ethanol / -90 - 20 °C View Scheme

1.1: 75 percent / K2CO3 / acetone / 6 h / Heating 2.1: 76 percent / I2 / dimethylsulfoxide / 24 h / 110 °C 3.1: DMSO; 3 Angstroem molecular sieves / acetone; CH2Cl2 / -20 - 0 °C 3.2: 50 percent / TsOH*H2O / CH2Cl2 / 1 h / 20 °C 4.1: 85 percent / PPh3 / Pd2(dba)3*CHCl3 / CH2Cl2 / 3 h / 0 °C 5.1: 73 percent / NaBH4 / CH2Cl2; methanol / 3 h / -78 °C 6.1: 156 mg / pyridine; DMAP / CH2Cl2 / 1 h / 0 °C 7.1: 77 percent / OsO4; NMO / 2-methyl-propan-2-ol; H2O / 24 h / 0 °C 8.1: p-TsOH*H2O / CH2Cl2 / 0.25 h / 0 °C 8.2: 99 percent / aq. HOAc / CH2Cl2 / 0.25 h / 0 °C 9.1: 62 percent / DBU / toluene / 1 h / 0 °C 10.1: 91 percent / DBU / toluene / 1 h / 0 °C View Scheme

1: iodine; pyridine / 5 h / 95 °C 2: N-bromosuccinmide / trifluoroacetic acid / 5 h / 20 °C 3: copper(I) bromide / methanol; N,N-dimethyl-formamide / 1 h / 120 °C / |Inert atmosphere; |Microwave irradiation View Scheme

sodium borohydride; sulfuric acid; acetic anhydride; sodium hydrogencarbonate in tetrahydrofuran; ethanol; water; acetic acid

hydrogenchloride; sodium cyanoborohydride in methanol 84 h; further solvent;