sodium periodate; calcium carbonate 1.) H2O, RT, 16 h, 2.) RT, 24 h,; Yield given. Multistep reaction;

ammonia; sodium in tetrahydrofuran T=-30°C; 3 h;

potassium hydroxide in ethanol T=110°C; 1.5 h;

potassium hydroxide

1: HgBr2 / 5 h / 95 °C / 5 Torr 2: 2.4 g / 0.01 percent NaOMe / methanol / 3 h / Ambient temperature 3: 840 mg / silver triflate, 2,4,6-collidine / CH2Cl2 / 5 h / 0 °C 4: 0.01 percent NaOMe / methanol / 3 h / Ambient temperature 5: NaH / dimethylformamide / 3 h / Ambient temperature 6: 45 percent / liq. NH3, Na metal / tetrahydrofuran / 3 h / -30 °C View Scheme

1: HgBr2 / 5 h / 95 °C / 5 Torr 2: 2.4 g / 0.01 percent NaOMe / methanol / 3 h / Ambient temperature 3: 840 mg / silver triflate, 2,4,6-collidine / CH2Cl2 / 5 h / 0 °C 4: 0.01 percent NaOMe / methanol / 3 h / Ambient temperature 5: NaH / dimethylformamide / 3 h / Ambient temperature 6: 45 percent / liq. NH3, Na metal / tetrahydrofuran / 3 h / -30 °C View Scheme

1: 840 mg / silver triflate, 2,4,6-collidine / CH2Cl2 / 5 h / 0 °C 2: 0.01 percent NaOMe / methanol / 3 h / Ambient temperature 3: NaH / dimethylformamide / 3 h / Ambient temperature 4: 45 percent / liq. NH3, Na metal / tetrahydrofuran / 3 h / -30 °C View Scheme

1: 2.4 g / 0.01 percent NaOMe / methanol / 3 h / Ambient temperature 2: 840 mg / silver triflate, 2,4,6-collidine / CH2Cl2 / 5 h / 0 °C 3: 0.01 percent NaOMe / methanol / 3 h / Ambient temperature 4: NaH / dimethylformamide / 3 h / Ambient temperature 5: 45 percent / liq. NH3, Na metal / tetrahydrofuran / 3 h / -30 °C View Scheme

1: NaH / dimethylformamide / 3 h / Ambient temperature 2: 45 percent / liq. NH3, Na metal / tetrahydrofuran / 3 h / -30 °C View Scheme

1: 0.01 percent NaOMe / methanol / 3 h / Ambient temperature 2: NaH / dimethylformamide / 3 h / Ambient temperature 3: 45 percent / liq. NH3, Na metal / tetrahydrofuran / 3 h / -30 °C View Scheme