1: H2 / Adams' platinum oxide / methanol 2: 63.7 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 1 h / Ambient temperature 3: 27.3 percent / n-BuLi / hexane; tetrahydrofuran / 1.) -20 deg C, 1 h, 2.) -20 deg C, 1 h; r.t., 1 h 4: 58.1 percent / H2 / palladium-charcoal / ethanol; hexane View Scheme

1: LiAlH4 / diethyl ether / 2 h 2: H2 / Adams' platinum oxide / methanol 3: 63.7 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 1 h / Ambient temperature 4: 27.3 percent / n-BuLi / hexane; tetrahydrofuran / 1.) -20 deg C, 1 h, 2.) -20 deg C, 1 h; r.t., 1 h 5: 58.1 percent / H2 / palladium-charcoal / ethanol; hexane View Scheme

1: diethyl ether 2: N-bromosuccinimide / 1,2-dimethoxy-ethane; H2O / Ambient temperature 3: MeONa / methanol / 0.5 h / Ambient temperature 4: 98 percent / periodic acid dihydrate / diethyl ether; tetrahydrofuran / 0.5 h / Ambient temperature 5: LiAlH4 / diethyl ether / 2 h 6: H2 / Adams' platinum oxide / methanol 7: 63.7 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 1 h / Ambient temperature 8: 27.3 percent / n-BuLi / hexane; tetrahydrofuran / 1.) -20 deg C, 1 h, 2.) -20 deg C, 1 h; r.t., 1 h 9: 58.1 percent / H2 / palladium-charcoal / ethanol; hexane View Scheme

1: N-bromosuccinimide / 1,2-dimethoxy-ethane; H2O / Ambient temperature 2: MeONa / methanol / 0.5 h / Ambient temperature 3: 98 percent / periodic acid dihydrate / diethyl ether; tetrahydrofuran / 0.5 h / Ambient temperature 4: LiAlH4 / diethyl ether / 2 h 5: H2 / Adams' platinum oxide / methanol 6: 63.7 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 1 h / Ambient temperature 7: 27.3 percent / n-BuLi / hexane; tetrahydrofuran / 1.) -20 deg C, 1 h, 2.) -20 deg C, 1 h; r.t., 1 h 8: 58.1 percent / H2 / palladium-charcoal / ethanol; hexane View Scheme

1: MeONa / methanol / 0.5 h / Ambient temperature 2: 98 percent / periodic acid dihydrate / diethyl ether; tetrahydrofuran / 0.5 h / Ambient temperature 3: LiAlH4 / diethyl ether / 2 h 4: H2 / Adams' platinum oxide / methanol 5: 63.7 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 1 h / Ambient temperature 6: 27.3 percent / n-BuLi / hexane; tetrahydrofuran / 1.) -20 deg C, 1 h, 2.) -20 deg C, 1 h; r.t., 1 h 7: 58.1 percent / H2 / palladium-charcoal / ethanol; hexane View Scheme

1: 98 percent / periodic acid dihydrate / diethyl ether; tetrahydrofuran / 0.5 h / Ambient temperature 2: LiAlH4 / diethyl ether / 2 h 3: H2 / Adams' platinum oxide / methanol 4: 63.7 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 1 h / Ambient temperature 5: 27.3 percent / n-BuLi / hexane; tetrahydrofuran / 1.) -20 deg C, 1 h, 2.) -20 deg C, 1 h; r.t., 1 h 6: 58.1 percent / H2 / palladium-charcoal / ethanol; hexane View Scheme

1: 82 percent / pyridine / 0 °C 2: 19 percent / CuI / diethyl ether / 1) cooling, 1 h, 2) warming to rt, 2 h, 3) rt, 15 h View Scheme

[2,2']bipyridinyl; copper(l) iodide in tetrahydrofuran 1) 2 deg C, 2 h, 2) rt, 20 h;

copper(l) iodide in diethyl ether 1) cooling, 1 h, 2) warming to rt, 2 h, 3) rt, 15 h;