pyridine; lead(IV) acetate; copper diacetate in benzene 2 h; Heating;

1: PBr3, pyridine / diethyl ether 2: 1a.) ethylmagnesium bromide, 1b.) cuprous chloride / 1a.) THF, reflux, 6 h, 1b.) 0 deg C, 15 min, 3.) reflux, 9 h 3: 66 percent / p-TsOH / methanol / 4 h / Heating 4: 92 percent / H2, quinoline / Lindlar's catalyst / hexane / Ambient temperature 5: 81 percent / triethylamine / CH2Cl2 / 0.5 h / -5 °C 6: 1.) Mg, iodine, 2.) HMPA / 1.) THF, 40-50 deg C, 1.5 h, 2.) 0-10 deg C, 30 min, 3.) RT, overnight View Scheme

1: 1a.) ethylmagnesium bromide, 1b.) cuprous chloride / 1a.) THF, reflux, 6 h, 1b.) 0 deg C, 15 min, 3.) reflux, 9 h 2: 66 percent / p-TsOH / methanol / 4 h / Heating 3: 92 percent / H2, quinoline / Lindlar's catalyst / hexane / Ambient temperature 4: 81 percent / triethylamine / CH2Cl2 / 0.5 h / -5 °C 5: 1.) Mg, iodine, 2.) HMPA / 1.) THF, 40-50 deg C, 1.5 h, 2.) 0-10 deg C, 30 min, 3.) RT, overnight View Scheme

1: 92 percent / H2, quinoline / Lindlar's catalyst / hexane / Ambient temperature 2: 81 percent / triethylamine / CH2Cl2 / 0.5 h / -5 °C 3: 1.) Mg, iodine, 2.) HMPA / 1.) THF, 40-50 deg C, 1.5 h, 2.) 0-10 deg C, 30 min, 3.) RT, overnight View Scheme

1: 66 percent / p-TsOH / methanol / 4 h / Heating 2: 92 percent / H2, quinoline / Lindlar's catalyst / hexane / Ambient temperature 3: 81 percent / triethylamine / CH2Cl2 / 0.5 h / -5 °C 4: 1.) Mg, iodine, 2.) HMPA / 1.) THF, 40-50 deg C, 1.5 h, 2.) 0-10 deg C, 30 min, 3.) RT, overnight View Scheme

1: 81 percent / triethylamine / CH2Cl2 / 0.5 h / -5 °C 2: 1.) Mg, iodine, 2.) HMPA / 1.) THF, 40-50 deg C, 1.5 h, 2.) 0-10 deg C, 30 min, 3.) RT, overnight View Scheme

N,N,N',N',N'',N''-hexamethylphosphoric triamide; iodine; magnesium 1.) THF, 40-50 deg C, 1.5 h, 2.) 0-10 deg C, 30 min, 3.) RT, overnight; Yield given. Multistep reaction;