1: 1.) Mg, I2, 1,2-dibromoethane / 1.) ether, reflux, 1 h, 2.) ether, 4 h 2: 91 percent / p-TsOH*H2O / toluene / 20 h / Heating 3: 1.) NaBH4, BF3*Et2O, 2.) NaOH, H2O2 / 1.) diglyme, a) 25 deg C, 1 h, b) 160 - 165 deg C, 2.5 h, 2.) diglyme, water, RT, 1.5 h 4: 1.) PPh3, 2.) NBS / 1.) DMF, CH2Cl2, 25 deg C, 10 min, 2.) DMF, CH2Cl2, from -78 to 25 deg C, 2 h 5: 96 percent / dimethylsulfoxide / 1.5 h / 25 °C 6: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, from -40 to -30 deg C, 1.5 h, 2.) THF, hexane, 25 deg C, 22 h 7: H2 / 10percent Pd/C View Scheme

1: 1.) PPh3, 2.) NBS / 1.) DMF, CH2Cl2, 25 deg C, 10 min, 2.) DMF, CH2Cl2, from -78 to 25 deg C, 2 h 2: 96 percent / dimethylsulfoxide / 1.5 h / 25 °C 3: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, from -40 to -30 deg C, 1.5 h, 2.) THF, hexane, 25 deg C, 22 h 4: H2 / 10percent Pd/C View Scheme

1: 96 percent / dimethylsulfoxide / 1.5 h / 25 °C 2: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, from -40 to -30 deg C, 1.5 h, 2.) THF, hexane, 25 deg C, 22 h 3: H2 / 10percent Pd/C View Scheme

1: 91 percent / p-TsOH*H2O / toluene / 20 h / Heating 2: 1.) NaBH4, BF3*Et2O, 2.) NaOH, H2O2 / 1.) diglyme, a) 25 deg C, 1 h, b) 160 - 165 deg C, 2.5 h, 2.) diglyme, water, RT, 1.5 h 3: 1.) PPh3, 2.) NBS / 1.) DMF, CH2Cl2, 25 deg C, 10 min, 2.) DMF, CH2Cl2, from -78 to 25 deg C, 2 h 4: 96 percent / dimethylsulfoxide / 1.5 h / 25 °C 5: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, from -40 to -30 deg C, 1.5 h, 2.) THF, hexane, 25 deg C, 22 h 6: H2 / 10percent Pd/C View Scheme

1: 1.) NaBH4, BF3*Et2O, 2.) NaOH, H2O2 / 1.) diglyme, a) 25 deg C, 1 h, b) 160 - 165 deg C, 2.5 h, 2.) diglyme, water, RT, 1.5 h 2: 1.) PPh3, 2.) NBS / 1.) DMF, CH2Cl2, 25 deg C, 10 min, 2.) DMF, CH2Cl2, from -78 to 25 deg C, 2 h 3: 96 percent / dimethylsulfoxide / 1.5 h / 25 °C 4: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, from -40 to -30 deg C, 1.5 h, 2.) THF, hexane, 25 deg C, 22 h 5: H2 / 10percent Pd/C View Scheme

1: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, from -40 to -30 deg C, 1.5 h, 2.) THF, hexane, 25 deg C, 22 h 2: H2 / 10percent Pd/C View Scheme

hydrogen; palladium on activated charcoal

1: (i) NaH, DMSO, (ii) /BRN= 2440576/ 2: Zn-Hg, aq. HCl / toluene / Heating View Scheme

1: aq. NaOH / ethanol 2: H2 / Pd-C / ethyl acetate 3: Zn-Hg, AcOH, aq. HCl View Scheme

1: H2 / Pd-C / ethyl acetate 2: Zn-Hg, AcOH, aq. HCl View Scheme