1: 1) n-BuLi / 1) THF, HMPA, 0 deg C, 10 min, 2) rt, overnight 2: 93 percent / H2, quinoline / Pd/C/CaCO3 / hexane / 760 Torr 3: 77 percent / p-TsOH*H2O / methanol / 2 h / Ambient temperature 4: 88 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature 5: 1) LDA / 1) THF, -10 deg C, 10 min, 2) -78 deg C -> 25 deg C 6: 55 percent / CH2Cl2 / Ambient temperature View Scheme

1: 91 percent / p-TsOH*H2O / CH2Cl2 / 3 h / 25 °C 2: 1) n-BuLi / 1) THF, HMPA, 0 deg C, 10 min, 2) rt, overnight 3: 93 percent / H2, quinoline / Pd/C/CaCO3 / hexane / 760 Torr 4: 77 percent / p-TsOH*H2O / methanol / 2 h / Ambient temperature 5: 88 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature 6: 1) LDA / 1) THF, -10 deg C, 10 min, 2) -78 deg C -> 25 deg C 7: 55 percent / CH2Cl2 / Ambient temperature View Scheme

in dichloromethane Ambient temperature;