1: 1.) n-BuLi / 1.) THF, -78 deg C, 1h, then 0 deg C, 2h, 2.) 0 deg C, 18h 2: Raney Ni / ethanol / 16 h 3: barium permanganate / CH2Cl2 / 16 h 5: O2, rose bengal / CH2Cl2; methanol / -78 °C / Irradiation 6: 2N hydrochloric acid / tetrahydrofuran / 2 h / Ambient temperature 7: Irradiation View Scheme

n-butyllithium in tetrahydrofuran T=0°C; 12 h;

n-butyllithium in various solvent(s) T=0°C; Yield given. Yields of byproduct given;

sulfenylation of the dilithio-derivative;

1: 1.) n-BuLi / 1.) THF, -78 deg C, 1h, then 0 deg C, 2h, 2.) 0 deg C, 18h 2: Raney Ni / ethanol / 16 h 3: barium permanganate / CH2Cl2 / 16 h View Scheme

1H-imidazole in N,N-dimethyl-formamide 12 h; Ambient temperature;

1: 90 percent / imidazole / dimethylformamide / 12 h / Ambient temperature 2: 88 percent / BuLi / diethyl ether / 48 h / 0 °C 3: 90 percent / Raney nickel / ethanol / 6 h / Heating 4: 75 percent / HOOAc, NaOAc / CH2Cl2 / 3.5 h / 7 °C View Scheme

2: 56 percent / H2 / Raney nickel / ethanol / Heating 3: 77 percent / MsCl, LiCl, s-collidine / dimethylformamide View Scheme