1: 70 percent / Br2, AcOH / 16 h / Ambient temperature 2: 1.) conc HCl, NaNO2, 2.) 50 percent H3PO2 / 1.) from -10 deg C to 0 deg C, 2 h, 2.) RT, overnight 3: 93 percent / conc. HCl / 16 h / Heating 4: DIBAL-H / toluene / 0.67 h / Heating 6: HOBT, DEC / dimethylformamide / 24 h / 25 °C 7: TFA / CH2Cl2 / 24 h / 25 °C 8: 82 percent / CH2Cl2 / 48 h / 25 °C View Scheme

1: 85 percent / iron filings, CaCl2, H2O / ethanol / 16 h / Heating 2: 70 percent / Br2, AcOH / 16 h / Ambient temperature 3: 1.) conc HCl, NaNO2, 2.) 50 percent H3PO2 / 1.) from -10 deg C to 0 deg C, 2 h, 2.) RT, overnight 4: 93 percent / conc. HCl / 16 h / Heating 5: DIBAL-H / toluene / 0.67 h / Heating 7: HOBT, DEC / dimethylformamide / 24 h / 25 °C 8: TFA / CH2Cl2 / 24 h / 25 °C 9: 82 percent / CH2Cl2 / 48 h / 25 °C View Scheme

1: 1.) conc HCl, NaNO2, 2.) 50 percent H3PO2 / 1.) from -10 deg C to 0 deg C, 2 h, 2.) RT, overnight 2: 93 percent / conc. HCl / 16 h / Heating 3: DIBAL-H / toluene / 0.67 h / Heating 5: HOBT, DEC / dimethylformamide / 24 h / 25 °C 6: TFA / CH2Cl2 / 24 h / 25 °C 7: 82 percent / CH2Cl2 / 48 h / 25 °C View Scheme

1.1: 84 percent / zinc dust; acetic anhydride; trifluoroacetic acid / tetrahydrofuran / 24 h / -25 - 18 °C 2.1: lithium diisopropylamide*THF; quinine; water / toluene; cyclohexane / 21 h / 5 - 25 °C 2.2: 10.5 g / sulfuric acid / toluene / 4 h / 85 °C 3.1: 80 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide; toluene / 18 h / 20 °C 4.1: hydrochloric acid / ethanol / 6 h / 20 °C 5.1: 5.44 g / NaOH / ethanol; 1-methyl-pyrrolidin-2-one / 10 h / 110 °C / pH 9 View Scheme

1.1: lithium diisopropylamide*THF; quinine; water / toluene; cyclohexane / 21 h / 5 - 25 °C 1.2: 10.5 g / sulfuric acid / toluene / 4 h / 85 °C 2.1: 80 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide; toluene / 18 h / 20 °C 3.1: hydrochloric acid / ethanol / 6 h / 20 °C 4.1: 5.44 g / NaOH / ethanol; 1-methyl-pyrrolidin-2-one / 10 h / 110 °C / pH 9 View Scheme