hydrogen; palladium on activated charcoal in ethanol; hexane

1: 1) Mg / 2) CuI, 2,2'-bipyridyl / 1) THF, 2) THF, 2 deg C, 2 h, then rt, 20 h 2: 1) diborane, 2) Br2, NaOMe / 1) THF, 0 deg C, 0.5 h, then 20 deg C, 0.5 h, 2) MeOH 3: 34 percent / CuI, 2,2'-bipyridyl / tetrahydrofuran / 1) 2 deg C, 2 h, 2) rt, 20 h View Scheme

1: 1) diborane, 2) Br2, NaOMe / 1) THF, 0 deg C, 0.5 h, then 20 deg C, 0.5 h, 2) MeOH 2: 34 percent / CuI, 2,2'-bipyridyl / tetrahydrofuran / 1) 2 deg C, 2 h, 2) rt, 20 h View Scheme

1: xylene / 96 h / Heating 2: 27.3 percent / n-BuLi / hexane; tetrahydrofuran / 1.) -20 deg C, 1 h, 2.) -20 deg C, 1 h; r.t., 1 h 3: 58.1 percent / H2 / palladium-charcoal / ethanol; hexane View Scheme

1: 48percent hydrobromic acid / 2 h / 5 - 10 °C 2: dimethylformamide / 48 h / Ambient temperature 3: KOH / aq. ethanol / 48 h / Heating 4: diethyl ether 5: N-bromosuccinimide / 1,2-dimethoxy-ethane; H2O / Ambient temperature 6: MeONa / methanol / 0.5 h / Ambient temperature 7: 98 percent / periodic acid dihydrate / diethyl ether; tetrahydrofuran / 0.5 h / Ambient temperature 8: LiAlH4 / diethyl ether / 2 h 9: H2 / Adams' platinum oxide / methanol 10: 63.7 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 1 h / Ambient temperature 11: 27.3 percent / n-BuLi / hexane; tetrahydrofuran / 1.) -20 deg C, 1 h, 2.) -20 deg C, 1 h; r.t., 1 h 12: 58.1 percent / H2 / palladium-charcoal / ethanol; hexane View Scheme

1: 27.3 percent / n-BuLi / hexane; tetrahydrofuran / 1.) -20 deg C, 1 h, 2.) -20 deg C, 1 h; r.t., 1 h 2: 58.1 percent / H2 / palladium-charcoal / ethanol; hexane View Scheme

1: KOH / aq. ethanol / 48 h / Heating 2: diethyl ether 3: N-bromosuccinimide / 1,2-dimethoxy-ethane; H2O / Ambient temperature 4: MeONa / methanol / 0.5 h / Ambient temperature 5: 98 percent / periodic acid dihydrate / diethyl ether; tetrahydrofuran / 0.5 h / Ambient temperature 6: LiAlH4 / diethyl ether / 2 h 7: H2 / Adams' platinum oxide / methanol 8: 63.7 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 1 h / Ambient temperature 9: 27.3 percent / n-BuLi / hexane; tetrahydrofuran / 1.) -20 deg C, 1 h, 2.) -20 deg C, 1 h; r.t., 1 h 10: 58.1 percent / H2 / palladium-charcoal / ethanol; hexane View Scheme

1: dimethylformamide / 48 h / Ambient temperature 2: KOH / aq. ethanol / 48 h / Heating 3: diethyl ether 4: N-bromosuccinimide / 1,2-dimethoxy-ethane; H2O / Ambient temperature 5: MeONa / methanol / 0.5 h / Ambient temperature 6: 98 percent / periodic acid dihydrate / diethyl ether; tetrahydrofuran / 0.5 h / Ambient temperature 7: LiAlH4 / diethyl ether / 2 h 8: H2 / Adams' platinum oxide / methanol 9: 63.7 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 1 h / Ambient temperature 10: 27.3 percent / n-BuLi / hexane; tetrahydrofuran / 1.) -20 deg C, 1 h, 2.) -20 deg C, 1 h; r.t., 1 h 11: 58.1 percent / H2 / palladium-charcoal / ethanol; hexane View Scheme

1: 63.7 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 1 h / Ambient temperature 2: 27.3 percent / n-BuLi / hexane; tetrahydrofuran / 1.) -20 deg C, 1 h, 2.) -20 deg C, 1 h; r.t., 1 h 3: 58.1 percent / H2 / palladium-charcoal / ethanol; hexane View Scheme

1: 27.3 percent / n-BuLi / hexane; tetrahydrofuran / 1.) -20 deg C, 1 h, 2.) -20 deg C, 1 h; r.t., 1 h 2: 58.1 percent / H2 / palladium-charcoal / ethanol; hexane View Scheme