silver-graphite; zinc in tetrahydrofuran T=-20 - 25°C; 0.333333 h;

1.1: 82 percent / 2,6-lutidine / nitromethane / 12 h / 25 °C 2.1: 99 percent / NaOMe; H2O / methanol / 1 h / 25 °C 3.1: NaH / tetrahydrofuran; various solvent(s) / 0.17 h / 25 °C 3.2: 98 percent / tetrabutylammonium iodide / tetrahydrofuran; various solvent(s) / 4 h / Heating 4.1: ZnCl2 / CH2Cl2; diethyl ether / 1 h / -60 - 0 °C 5.1: 3.4 g / NaOMe / methanol / 4 h / 25 °C 6.1: 97 percent / DMAP; Et3N / CH2Cl2 / 48 h / 25 °C 7.1: 88 percent / NBS; H2O / CH2Cl2 / 1 h / 25 °C 8.1: 95 percent / DBU / CH2Cl2 / 12 h / 25 °C 9.1: 93 percent / BF3*Et2O; molecular sieves 4 Angstroem / CH2Cl2 / -78 - -20 °C 10.1: 81 percent / NBS; H2O / CH2Cl2 / 2 h / 25 °C 11.1: 88 percent / DBU / CH2Cl2 / 12 h / 25 °C 12.1: 89 percent / TMSOTf; molecular sieves 4 Angstroem / CH2Cl2 / 5 h / -20 °C 13.1: DDQ / CH2Cl2; H2O / 12 h / 25 °C 13.2: 81 percent / Pd(CN)2Cl2 / acetone; H2O / 2 h / 25 °C View Scheme