1: 92 percent / H2, quinoline / Lindlar's catalyst / hexane; ethanol 2: 82 percent / Et3N / CH2Cl2 / 3 h 3: 2.) Li2CuCl4 / 1.) THF, 20 min, 2.) THF, a) -10 deg C, 3 h, b) RT, overnight 4: 78 percent / p-toluenesulphonic acid / methanol / 14 h / Ambient temperature 5: 66 percent / PCC / CH2Cl2 6: 69 percent / tetrahydrofuran / 4 h / 0 °C 7: 61 percent / PCC, NaOAc / CH2Cl2 View Scheme

1: With [PtCl2(H2C=CH2)]2 in 1,4-dioxane T=23°C; 0.5 h; 2: With camphor-10-sulfonic acid; acetonitrile in 1,4-dioxane T=20°C; 4 h; 3: With magnesium sulfate in 1,4-dioxane T=20°C; 5 h; Title compound not separated from byproducts;

1: 92 percent / H2, quinoline / Lindlar's catalyst / hexane; ethanol 2: 82 percent / Et3N / CH2Cl2 / 3 h 3: 57 percent / Li2CuCl4 / tetrahydrofuran / -10 °C 4: 1.) CBr4, 2.) Ph3P / 1.) CH2Cl2, RT, 10 min, 2.) CH2Cl2, RT, overnight 5: 56 percent / Li2CuCl4 / tetrahydrofuran / -10 °C 6: p-toluenesulphonic acid / methanol / 76 °C View Scheme

1: 92 percent / H2, quinoline / Lindlar's catalyst / hexane; ethanol 2: 82 percent / Et3N / CH2Cl2 / 3 h 3: 2.) Li2CuCl4 / 1.) THF, 20 min, 2.) THF, a) -10 deg C, 3 h, b) RT, overnight 4: 78 percent / p-toluenesulphonic acid / methanol / 14 h / Ambient temperature 5: 66 percent / PCC / CH2Cl2 View Scheme