pyridinium p-toluenesulfonate in methanol Ambient temperature;

potassium hydroxide; water in ethanol 5 h; Ambient temperature;

1: 48percent aq. HBr / H2O / 24 h / 80 °C 2: 95 percent / Amberlyst H-15 / hexane / 8 h / Ambient temperature 4: 94 percent / FeCl3 / diethyl ether / Ambient temperature 5: 1.) 1.6 M n-BuLi, 2.) ZnBr2, tetrakis triphenyl phosphine palladium (3percent) / 1.) Et2O, -60 deg C, 30 min, 2.) THF, RT 6: 2N KOH / methanol View Scheme

1: 95 percent / Amberlyst H-15 / hexane / 8 h / Ambient temperature 3: 94 percent / FeCl3 / diethyl ether / Ambient temperature 4: 1.) 1.6 M n-BuLi, 2.) ZnBr2, tetrakis triphenyl phosphine palladium (3percent) / 1.) Et2O, -60 deg C, 30 min, 2.) THF, RT 5: 2N KOH / methanol View Scheme

1: 1.) lithium amide / 1.) liquid NH3, THF, -33 deg C, 2 h, 2.) 6 h 2: pyridinium chlorochromate (PCC) / CH2Cl2 / 1 h 3: 1.) sodium hydride / 1.) THF, RT, 30 min, 2.) 2 h 4: LAH, ethanol / diethyl ether / 0.5 h / 0 °C 5: H2 / Lindlar's catalyst / hexane; ethanol 6: TEA / CH2Cl2 / 4 h / 0 °C 7: 1.) Mg, 2.) Li2CuCl3 / 1.) THF, 2.) 0 deg C, 3 h 8: 82 percent / PTS / methanol / Ambient temperature View Scheme

1: 1.) sodium hydride / 1.) THF, RT, 30 min, 2.) 2 h 2: LAH, ethanol / diethyl ether / 0.5 h / 0 °C 3: H2 / Lindlar's catalyst / hexane; ethanol 4: TEA / CH2Cl2 / 4 h / 0 °C 5: 1.) Mg, 2.) Li2CuCl3 / 1.) THF, 2.) 0 deg C, 3 h 6: 82 percent / PTS / methanol / Ambient temperature View Scheme

1: pyridinium chlorochromate (PCC) / CH2Cl2 / 1 h 2: 1.) sodium hydride / 1.) THF, RT, 30 min, 2.) 2 h 3: LAH, ethanol / diethyl ether / 0.5 h / 0 °C 4: H2 / Lindlar's catalyst / hexane; ethanol 5: TEA / CH2Cl2 / 4 h / 0 °C 6: 1.) Mg, 2.) Li2CuCl3 / 1.) THF, 2.) 0 deg C, 3 h 7: 82 percent / PTS / methanol / Ambient temperature View Scheme

1: H2 / Lindlar's catalyst / hexane; ethanol 2: TEA / CH2Cl2 / 4 h / 0 °C 3: 1.) Mg, 2.) Li2CuCl3 / 1.) THF, 2.) 0 deg C, 3 h 4: 82 percent / PTS / methanol / Ambient temperature View Scheme

1: LAH, ethanol / diethyl ether / 0.5 h / 0 °C 2: H2 / Lindlar's catalyst / hexane; ethanol 3: TEA / CH2Cl2 / 4 h / 0 °C 4: 1.) Mg, 2.) Li2CuCl3 / 1.) THF, 2.) 0 deg C, 3 h 5: 82 percent / PTS / methanol / Ambient temperature View Scheme

1: 1.) MeLi / 1.) hexane, Et2O, a) -78 deg C, 2 h, b) -20 deg C, 15 min, 2.) hexane, Et2O, a) -78 deg C, 0.5 h, b) 25 deg C, 2 h 2: 79 percent / diisobutylaluminum hydride / diethyl ether / 3.33 h / 25 - 40 °C 3: pyridine, NBS / diethyl ether / 1.25 h / 25 - 30 °C / Irradiation 4: 1.) Br2, 2.) tetrabutylammonium fluoride trihydrate / 1.) CH2Cl2, -78 deg C, 2.) THF, CH2Cl2, -20 deg C 5: 85 percent / EtONa, BHA, Pd(PPh3)4 / toluene; ethanol / 0.75 h / 65 °C 6: pyridinium tosylate, BHA, / ethanol / 3 h / 45 °C View Scheme