1: 1.) MeSO2Cl, Et3N, 2.) LiBr / 1.) CH2Cl2, r.t., 3 h, 2.) acetone, r.t., 5 h 2: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 30 min, 2.) THF, r.t., 2 h 3: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 30 min, 2.) THF, r.t., 2 h 4: 73 percent / silica gel / tetrahydrofuran; H2O / 5 h / 25 °C 5: 22 percent / hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 3 h / Heating 6: 92 percent / 5percent aq. HCl / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: 1) trifluoroacetic anhydride, 2) LiBr / 1) THF, 0-5 deg C, 45 min, 2) THF, DMF, 80 deg C, overnight 2: 1a) Mg / 1b) (tpp)2NiCl2 / 1a) ether, 30 deg C, 1 h, 1b) benzene, 10 min, 2) r.t., 72 h 3: 1) trifluoroacetic anhydride, 2) LiBr / 1) THF, 0-5 deg C, 45 min, 2) THF, DMF, 80 deg C, overnight 4: 1) Mg, 2) LiCuCl4 / 1) ether, 2 h, 2) THF, 0 deg C, 3.75 h View Scheme

hydrogen; palladium on activated charcoal in ethyl acetate P=760.051 Torr; 1 h;

1: 1.) MeSO2Cl, Et3N, 2.) LiBr / 1.) CH2Cl2, r.t., 3 h, 2.) acetone, r.t., 5 h 2: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 30 min, 2.) THF, r.t., 2 h 3: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 30 min, 2.) THF, r.t., 2 h 4: 73 percent / silica gel / tetrahydrofuran; H2O / 5 h / 25 °C 5: 22 percent / hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 3 h / Heating 6: 92 percent / 5percent aq. HCl / tetrahydrofuran / 1 h / Ambient temperature 7: 86 percent / pyridine / 5 h / 0 °C View Scheme

acetic acid T=170°C;

in dichloromethane Acetylation;

N-bromosuccinmide; triphenylphosphine in DMF (N,N-dimethyl-formamide) T=20°C; 0.5 h;

1: 83 percent / Br2, triphenylphosphine / CCl4 / 1 h / Ambient temperature 2: 1.) Li, ferric chloride, liquid ammonia / 1.) THF, 1 h, 2.) DMSO, -35 deg C, 3 h 3: TsOH, H2O / methanol / 24 h / Ambient temperature View Scheme