1: H2 / 10percent Pd/C / 4 h / 20 °C / 760 Torr 2: 1.) diethoxytriphenylphosphorane; 2.) DMAP / 1.) toluene, 20-40 degC, 24 h; 2.) MeCN 3: 50 percent / CuBr*Me2S / toluene / 4 h / -50 °C 4: trifluoroacetic acid View Scheme

nitric acid in dichloromethane T=0°C; nitrolysis; 2 h;

1: H2 / 10percent Pd/C / 4 h / 20 °C / 760 Torr 2: 1.) diethoxytriphenylphosphorane; 2.) DMAP / 1.) toluene, 20-40 degC, 24 h; 2.) MeCN 3: 83 percent / CuBr*Me2S / toluene / 1 h / -20 °C 4: trifluoroacetic acid View Scheme

1: H2 / 10percent Pd/C / 4 h / 20 °C / 760 Torr 2: 1.) diethoxytriphenylphosphorane; 2.) DMAP / 1.) toluene, 20-40 degC, 24 h; 2.) MeCN View Scheme

1: 89 percent / 100 percent HNO3 / CH2Cl2 / 2 h / 0 °C 2: 80 percent / 96 percent H2SO4 / CH2Cl2 / -25 - 20 °C 3: 47 percent / 100 percent HNO3 / CH2Cl2 / 2 h / 0 °C View Scheme

1: 89 percent / 100 percent HNO3 / CH2Cl2 / 2 h / 0 °C 2: 80 percent / 96 percent H2SO4 / CH2Cl2 / -25 - 20 °C View Scheme