1: 96 percent / NaBH4, CeCl3*7H2O / methanol / 0.08 h / 0 °C 2: 89 percent / CBr4, PPh3 / pyridine / 12 h / 0 °C 3: 80 percent / Zn, CuI / aq. ethanol / sonication 4: 1.) MnO2; 2.) p-TsOH / 1.) pentane, 24 h; 2.) THF, reflux, 4 h View Scheme

1: 96 percent / NaBH4, CeCl3*7H2O / methanol / 0.08 h / 0 °C 2: 89 percent / CBr4, PPh3 / pyridine / 12 h / 0 °C 3: 80 percent / Zn, CuI / aq. ethanol / sonication 4: 1.) MnO2; 2.) p-TsOH / 1.) pentane, 24 h; 2.) THF, reflux, 4 h View Scheme