1: 1.) HBr, 2.) KOH / 1.) glacial acetic acid, 0 deg C, 5 min, 2.) methanol, 15 min 2: 1.) BuLi, 2.) BF3*Et2O / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, -78 deg C, 1.5 h 3: H2 / Lindlar cat. / ethyl acetate 4: p-toluenesulfonic acid hydrate / toluene; H2O / 1 h / Heating View Scheme

1: aq. concd. HCl / methanol / 48 h / 20 °C 2: 1.) HBr, 2.) KOH / 1.) glacial acetic acid, 0 deg C, 5 min, 2.) methanol, 15 min 3: 1.) BuLi, 2.) BF3*Et2O / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, -78 deg C, 1.5 h 4: H2 / Lindlar cat. / ethyl acetate 5: p-toluenesulfonic acid hydrate / toluene; H2O / 1 h / Heating View Scheme

1: 1.) Mg, 2.) Li2CuCl4 / 1.) ether, THF, 2.) THF, -78 to -55 deg C, 1 h 2: aq. concd. HCl / methanol / 48 h / 20 °C 3: 1.) HBr, 2.) KOH / 1.) glacial acetic acid, 0 deg C, 5 min, 2.) methanol, 15 min 4: 1.) BuLi, 2.) BF3*Et2O / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, -78 deg C, 1.5 h 5: H2 / Lindlar cat. / ethyl acetate 6: p-toluenesulfonic acid hydrate / toluene; H2O / 1 h / Heating View Scheme

1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 2: 73 percent / quinoline; hydrogen / palladium on BaSO4 / ethyl acetate / 3 h / 20 °C / 750.06 Torr 3: 82 percent / triethylamine / CH2Cl2 / 0 - 20 °C 4: 78 percent / bis(tricyclohexylphosphine) benzylidene Ru(IV) dichloride / CH2Cl2 / 6 h / Heating View Scheme

1.1: 96 percent / hydrogen / [RuBr2((R)-SYNPHOS)] / 0.5 h / 50 °C / 7500.6 Torr 2.1: 94 percent / 2,6-lutidine / CH2Cl2 / 0.75 h / -25 - -15 °C 3.1: 71 percent / diisobutylaluminium hydride / CH2Cl2 / 3.5 h / -78 °C 4.1: LDA / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C 4.2: 87 percent / tetrahydrofuran; diethyl ether / 3 h / -78 - 0 °C 5.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 6.1: 73 percent / quinoline; hydrogen / palladium on BaSO4 / ethyl acetate / 3 h / 20 °C / 750.06 Torr 7.1: 82 percent / triethylamine / CH2Cl2 / 0 - 20 °C 8.1: 78 percent / bis(tricyclohexylphosphine) benzylidene Ru(IV) dichloride / CH2Cl2 / 6 h / Heating View Scheme

1.1: 94 percent / 2,6-lutidine / CH2Cl2 / 0.75 h / -25 - -15 °C 2.1: 71 percent / diisobutylaluminium hydride / CH2Cl2 / 3.5 h / -78 °C 3.1: LDA / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C 3.2: 87 percent / tetrahydrofuran; diethyl ether / 3 h / -78 - 0 °C 4.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 5.1: 73 percent / quinoline; hydrogen / palladium on BaSO4 / ethyl acetate / 3 h / 20 °C / 750.06 Torr 6.1: 82 percent / triethylamine / CH2Cl2 / 0 - 20 °C 7.1: 78 percent / bis(tricyclohexylphosphine) benzylidene Ru(IV) dichloride / CH2Cl2 / 6 h / Heating View Scheme

1.1: N,N'-carbonyldiimidazole / tetrahydrofuran / 8 h / 20 °C 1.2: 62 percent / tetrahydrofuran / 36 h / 20 °C 2.1: 96 percent / hydrogen / [RuBr2((R)-SYNPHOS)] / 0.5 h / 50 °C / 7500.6 Torr 3.1: 94 percent / 2,6-lutidine / CH2Cl2 / 0.75 h / -25 - -15 °C 4.1: 71 percent / diisobutylaluminium hydride / CH2Cl2 / 3.5 h / -78 °C 5.1: LDA / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C 5.2: 87 percent / tetrahydrofuran; diethyl ether / 3 h / -78 - 0 °C 6.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 7.1: 73 percent / quinoline; hydrogen / palladium on BaSO4 / ethyl acetate / 3 h / 20 °C / 750.06 Torr 8.1: 82 percent / triethylamine / CH2Cl2 / 0 - 20 °C 9.1: 78 percent / bis(tricyclohexylphosphine) benzylidene Ru(IV) dichloride / CH2Cl2 / 6 h / Heating View Scheme

1: NaOH / ethanol; H2O / 1 h / Heating 2: benzene / 1.5 h / Heating View Scheme

hydrogenchloride in methanol Ambient temperature; Yield given;

1: 92 percent / m-CPBA / CH2Cl2 / 10 h / 0 - 20 °C 2: 45 percent / (R,R)-salen-Co-OAc; water / 16 h / 0 °C 3: 86 percent / ethylene diamine / dimethylsulfoxide / 12 h / 20 °C 4: 92 percent / hydrogen; Pd/BaSO4; quinoline / benzene / 0.5 h / 20 °C / 750.08 Torr 5: 89 percent / Et3N / CH2Cl2 / 0 °C 6: 84 percent / (PCy3)2Ru(Cl)2=CH-Ph; Ti(i-PrO)4 / CH2Cl2 / 12 h / Heating View Scheme