n-butyllithium

1: 84 percent / i-Pr2NEt, Pd(OAc)2, Ph3P / dimethylformamide / 14 h / 80 °C 2: 1.) O3, 2.) NaBH4 / 1.) CH2Cl2, -78 deg C, 2.) MeOH, RT, 12 h 3: 76 percent / lipase / diethyl ether / 6 h / Ambient temperature 4: 74 percent / Et3N, 4-DMAP / CH2Cl2 / 3 h / Ambient temperature 5: 35 percent / NaBH4 / dimethylsulfoxide / 12 h / 60 °C 6: 54 percent / CrO3, H2SO4 / acetone / 0.5 h / 0 °C View Scheme

iron(II) sulfate in ammonia 1.5 h;

[I(py)2]BF4; trifluorormethanesulfonic acid in dichloromethane 0.5 h; Ambient temperature;

triethylsilane; trifluoroacetic acid T=50°C; 12 h;

Sandmeyer transformation;

1: diethyl ether; tetrahydrofuran / 12 h / 0 - 20 °C 2: trifluoroacetic acid; triethylsilane / 12 h / 50 °C View Scheme