1.1: N-bromosuccinimide / tetrahydrofuran; H2O / 17 h / 20 °C 2.1: KOH / H2O; methanol / 48 h / 90 °C 2.2: tetrahydrofuran; H2O / 14 h / 20 °C / pH 10.5 3.1: H2 / Pd/C / methanol / 18 h / 20 °C / 1500.15 Torr 4.1: triethylamine / methanol / 5 - 20 °C View Scheme

1: H2 / Pd/C / methanol / 18 h / 20 °C / 1500.15 Torr 2: triethylamine / methanol / 5 - 20 °C View Scheme

triethylamine in methanol T=5 - 20°C;

1.1: KOH / H2O; methanol / 48 h / 90 °C 1.2: tetrahydrofuran; H2O / 14 h / 20 °C / pH 10.5 2.1: H2 / Pd/C / methanol / 18 h / 20 °C / 1500.15 Torr 3.1: triethylamine / methanol / 5 - 20 °C View Scheme

1.1: KOH / H2O; methanol / 48 h / 90 °C 1.2: tetrahydrofuran; H2O / 14 h / 20 °C / pH 10.5 2.1: H2 / Pd/C / methanol / 18 h / 20 °C / 1500.15 Torr 3.1: triethylamine / methanol / 5 - 20 °C View Scheme

1.1: 85 percent / SOCl2 / 2 h / 0 - 20 °C 2.1: 96 percent / NEt3 / CH2Cl2 / 2 h / 0 °C 3.1: NBS / tetrahydrofuran; H2O / 20 °C 4.1: KOH / methanol; H2O / 90 °C 4.2: H2O; tetrahydrofuran / 5 - 20 °C / pH 10.5 5.1: H2 / Pd/C / methanol / 20 °C / 1810.02 Torr 6.1: NEt3 / methanol / 5 - 20 °C View Scheme

1.1: lactamase / Enzymatic reaction 2.1: 85 percent / SOCl2 / 2 h / 0 - 20 °C 3.1: 96 percent / NEt3 / CH2Cl2 / 2 h / 0 °C 4.1: NBS / tetrahydrofuran; H2O / 20 °C 5.1: KOH / methanol; H2O / 90 °C 5.2: H2O; tetrahydrofuran / 5 - 20 °C / pH 10.5 6.1: H2 / Pd/C / methanol / 20 °C / 1810.02 Torr 7.1: NEt3 / methanol / 5 - 20 °C View Scheme

1.1: triethylamine; DMAP / CH2Cl2 / 0.75 h / 0 °C 2.1: KOAc / dimethylformamide / 72 h / 60 °C 2.2: NaOMe / methanol / 7 h / 0 °C View Scheme