in toluene 1 h; Heating;

pyridine-2,6-dicarboxylic acid; ammonium cerium(IV) nitrate in water; acetonitrile a.) 20 min, 0 deg C b.) 10 min, RT;

1: t-BuOK / tetrahydrofuran; dimethylformamide / 2 h / -25 °C 2: 12.64 g / 4 h / 100 °C / 6 Torr View Scheme

1: 99 percent / AcOH / 24 h / 20 °C 2: t-BuOK / tetrahydrofuran; dimethylformamide / 2 h / -25 °C 3: 12.64 g / 4 h / 100 °C / 6 Torr View Scheme

1: t-BuOK / tetrahydrofuran; dimethylformamide / 2 h / -25 °C 2: 12.64 g / 4 h / 100 °C / 6 Torr View Scheme

1: 3,7-dimethylocta-2,6-dienyl bromide With tributyltin chloride; magnesium in tetrahydrofuran T=0°C; Barbier cross-coupling; 1.08333 h; 2: 2,3-Dimethoxy-5-methyl-1,4-benzoquinone With boron trifluoride diethyl etherate in dichloromethane T=-78 - 20°C; 2 h; 3: With iron(III) chloride in diethyl ether; water 0.5 h; Heating;

iron(III) chloride

1: 82 percent / molecular sieves 4 Angstroem / Amberlite IR 120-plus / benzene / Heating 2: K2CO3 / Bu4NHSO4 / acetone / 24 h / Heating 3: TsOH / methanol; H2O / 16 h / Ambient temperature 4: 91 percent / K2CO3 / acetone / 15 h / Heating 5: 96 percent / H2 / 10percent Pd/C / tetrahydrofuran / 6 h / Ambient temperature 6: 92 percent / K2(SO3)2NO, KH2SO4 / benzene; H2O / 3 h / Ambient temperature 7: 100 percent / CH2Cl2 / 96 h / Ambient temperature 8: 1.) KOBu-t / 1.) Et2O, -40 deg C, 30 min, 2.) Et2O, -70 deg C to room temp. 9: 100 percent / 3 h / 80 °C / 7.5 Torr View Scheme

1: 96 percent / 57percent HI, 30percent aq. H3PO2 / Heating 2: 82 percent / molecular sieves 4 Angstroem / Amberlite IR 120-plus / benzene / Heating 3: K2CO3 / Bu4NHSO4 / acetone / 24 h / Heating 4: TsOH / methanol; H2O / 16 h / Ambient temperature 5: 91 percent / K2CO3 / acetone / 15 h / Heating 6: 96 percent / H2 / 10percent Pd/C / tetrahydrofuran / 6 h / Ambient temperature 7: 92 percent / K2(SO3)2NO, KH2SO4 / benzene; H2O / 3 h / Ambient temperature 8: 100 percent / CH2Cl2 / 96 h / Ambient temperature 9: 1.) KOBu-t / 1.) Et2O, -40 deg C, 30 min, 2.) Et2O, -70 deg C to room temp. 10: 100 percent / 3 h / 80 °C / 7.5 Torr View Scheme

1: 97 percent / H2 / 10percent Pd/C / acetic acid / 72 h / 30002.4 Torr / Ambient temperature 2: 96 percent / 57percent HI, 30percent aq. H3PO2 / Heating 3: 82 percent / molecular sieves 4 Angstroem / Amberlite IR 120-plus / benzene / Heating 4: K2CO3 / Bu4NHSO4 / acetone / 24 h / Heating 5: TsOH / methanol; H2O / 16 h / Ambient temperature 6: 91 percent / K2CO3 / acetone / 15 h / Heating 7: 96 percent / H2 / 10percent Pd/C / tetrahydrofuran / 6 h / Ambient temperature 8: 92 percent / K2(SO3)2NO, KH2SO4 / benzene; H2O / 3 h / Ambient temperature 9: 100 percent / CH2Cl2 / 96 h / Ambient temperature 10: 1.) KOBu-t / 1.) Et2O, -40 deg C, 30 min, 2.) Et2O, -70 deg C to room temp. 11: 100 percent / 3 h / 80 °C / 7.5 Torr View Scheme