1.1: chiral chloronitroso synthon / CH2Cl2 / 12 h / 0 °C 1.2: 85 percent / Al-Hg / acetonitrile; H2O / 1.5 h / 20 °C 2.1: Et3N / acetonitrile / 8 h / 25 °C 3.1: 3.78 g / DBU / acetonitrile / 9 h / 25 °C 4.1: NBS / H2O; acetone / 10 h / 20 °C 4.2: 88 percent / K2CO3 / acetonitrile / 4 h / 60 °C 5.1: SnCl4 / CH2Cl2 / 0.33 h / 25 °C 5.2: 98 percent / DMAP; K2CO3; pyridine / CH2Cl2 / 6 h / 25 °C 6.1: 78 percent / mercaptoacetic acid; LiOH / dimethylformamide / 1 h / 25 °C 7.1: acetonitrile / 4 h / 25 °C 8.1: 0.24 g / NaIO4; RuCl3 / CCl4; acetonitrile; H2O / 3 h / 25 °C 9.1: 96 percent / DBU / benzene / 40 h / 70 °C 10.1: HCO2H / tetrahydrofuran / 45 h / 60 °C 10.2: 65 percent / LiAlH4 / tetrahydrofuran / 12 h / 25 °C View Scheme

1.1: K2CO3 / acetonitrile / 2 h / 85 °C 2.1: NaBH4 / methanol / 0 - 25 °C 3.1: HBr / CH2Cl2; H2O / 25 °C 4.1: NBS / H2O; acetone / 10 h / 20 °C 4.2: 88 percent / K2CO3 / acetonitrile / 4 h / 60 °C 5.1: SnCl4 / CH2Cl2 / 0.33 h / 25 °C 5.2: 98 percent / DMAP; K2CO3; pyridine / CH2Cl2 / 6 h / 25 °C 6.1: 78 percent / mercaptoacetic acid; LiOH / dimethylformamide / 1 h / 25 °C 7.1: acetonitrile / 4 h / 25 °C 8.1: 0.24 g / NaIO4; RuCl3 / CCl4; acetonitrile; H2O / 3 h / 25 °C 9.1: 96 percent / DBU / benzene / 40 h / 70 °C 10.1: HCO2H / tetrahydrofuran / 45 h / 60 °C 10.2: 65 percent / LiAlH4 / tetrahydrofuran / 12 h / 25 °C View Scheme

1.1: Et3N / acetonitrile / 8 h / 25 °C 2.1: 3.78 g / DBU / acetonitrile / 9 h / 25 °C 3.1: NBS / H2O; acetone / 10 h / 20 °C 3.2: 88 percent / K2CO3 / acetonitrile / 4 h / 60 °C 4.1: SnCl4 / CH2Cl2 / 0.33 h / 25 °C 4.2: 98 percent / DMAP; K2CO3; pyridine / CH2Cl2 / 6 h / 25 °C 5.1: 78 percent / mercaptoacetic acid; LiOH / dimethylformamide / 1 h / 25 °C 6.1: acetonitrile / 4 h / 25 °C 7.1: 0.24 g / NaIO4; RuCl3 / CCl4; acetonitrile; H2O / 3 h / 25 °C 8.1: 96 percent / DBU / benzene / 40 h / 70 °C 9.1: HCO2H / tetrahydrofuran / 45 h / 60 °C 9.2: 65 percent / LiAlH4 / tetrahydrofuran / 12 h / 25 °C View Scheme

1.1: NBS / H2O; acetone / 10 h / 20 °C 1.2: 88 percent / K2CO3 / acetonitrile / 4 h / 60 °C 2.1: SnCl4 / CH2Cl2 / 0.33 h / 25 °C 2.2: 98 percent / DMAP; K2CO3; pyridine / CH2Cl2 / 6 h / 25 °C 3.1: 78 percent / mercaptoacetic acid; LiOH / dimethylformamide / 1 h / 25 °C 4.1: acetonitrile / 4 h / 25 °C 5.1: 0.24 g / NaIO4; RuCl3 / CCl4; acetonitrile; H2O / 3 h / 25 °C 6.1: 96 percent / DBU / benzene / 40 h / 70 °C 7.1: HCO2H / tetrahydrofuran / 45 h / 60 °C 7.2: 65 percent / LiAlH4 / tetrahydrofuran / 12 h / 25 °C View Scheme

1.1: NaBH4 / methanol / 0 - 25 °C 2.1: HBr / CH2Cl2; H2O / 25 °C 3.1: NBS / H2O; acetone / 10 h / 20 °C 3.2: 88 percent / K2CO3 / acetonitrile / 4 h / 60 °C 4.1: SnCl4 / CH2Cl2 / 0.33 h / 25 °C 4.2: 98 percent / DMAP; K2CO3; pyridine / CH2Cl2 / 6 h / 25 °C 5.1: 78 percent / mercaptoacetic acid; LiOH / dimethylformamide / 1 h / 25 °C 6.1: acetonitrile / 4 h / 25 °C 7.1: 0.24 g / NaIO4; RuCl3 / CCl4; acetonitrile; H2O / 3 h / 25 °C 8.1: 96 percent / DBU / benzene / 40 h / 70 °C 9.1: HCO2H / tetrahydrofuran / 45 h / 60 °C 9.2: 65 percent / LiAlH4 / tetrahydrofuran / 12 h / 25 °C View Scheme

1.1: NBS / H2O; acetone / 10 h / 20 °C 1.2: 88 percent / K2CO3 / acetonitrile / 4 h / 60 °C 2.1: SnCl4 / CH2Cl2 / 0.33 h / 25 °C 2.2: 98 percent / DMAP; K2CO3; pyridine / CH2Cl2 / 6 h / 25 °C 3.1: 78 percent / mercaptoacetic acid; LiOH / dimethylformamide / 1 h / 25 °C 4.1: acetonitrile / 4 h / 25 °C 5.1: 0.24 g / NaIO4; RuCl3 / CCl4; acetonitrile; H2O / 3 h / 25 °C 6.1: 96 percent / DBU / benzene / 40 h / 70 °C 7.1: HCO2H / tetrahydrofuran / 45 h / 60 °C 7.2: 65 percent / LiAlH4 / tetrahydrofuran / 12 h / 25 °C View Scheme

1.1: acetonitrile / 4 h / 25 °C 2.1: 0.24 g / NaIO4; RuCl3 / CCl4; acetonitrile; H2O / 3 h / 25 °C 3.1: 96 percent / DBU / benzene / 40 h / 70 °C 4.1: HCO2H / tetrahydrofuran / 45 h / 60 °C 4.2: 65 percent / LiAlH4 / tetrahydrofuran / 12 h / 25 °C View Scheme

1.1: SnCl4 / CH2Cl2 / 0.33 h / 25 °C 1.2: 98 percent / DMAP; K2CO3; pyridine / CH2Cl2 / 6 h / 25 °C 2.1: 78 percent / mercaptoacetic acid; LiOH / dimethylformamide / 1 h / 25 °C 3.1: acetonitrile / 4 h / 25 °C 4.1: 0.24 g / NaIO4; RuCl3 / CCl4; acetonitrile; H2O / 3 h / 25 °C 5.1: 96 percent / DBU / benzene / 40 h / 70 °C 6.1: HCO2H / tetrahydrofuran / 45 h / 60 °C 6.2: 65 percent / LiAlH4 / tetrahydrofuran / 12 h / 25 °C View Scheme

1.1: 96 percent / DBU / benzene / 40 h / 70 °C 2.1: HCO2H / tetrahydrofuran / 45 h / 60 °C 2.2: 65 percent / LiAlH4 / tetrahydrofuran / 12 h / 25 °C View Scheme

1.1: 78 percent / mercaptoacetic acid; LiOH / dimethylformamide / 1 h / 25 °C 2.1: acetonitrile / 4 h / 25 °C 3.1: 0.24 g / NaIO4; RuCl3 / CCl4; acetonitrile; H2O / 3 h / 25 °C 4.1: 96 percent / DBU / benzene / 40 h / 70 °C 5.1: HCO2H / tetrahydrofuran / 45 h / 60 °C 5.2: 65 percent / LiAlH4 / tetrahydrofuran / 12 h / 25 °C View Scheme