1: Et3N / pyridine / 0 - 3 °C 2: aq. NH3 / H2O / 20 h / Ambient temperature; pH 8-9 3: 48 percent / H2, Dowex anion-exchange resin, KHCO3 / Pd black / propan-2-ol; H2O / 70 h / 70 °C / 19000 - 22800 Torr View Scheme

aeromonas hydrophila CECT 4221 T=45°C; pH=7; 16 h; aq. phosphate bufferEnzymatic reaction;

1: 98 percent / imidazole / dimethylformamide / 1 h / Ambient temperature 2: 1) lithium hexamethyldisilazide / 1) THF, -78 deg C, 1h, 2) room temperature, 30 min 3: tetrahydrofuran / -78 °C 4: DIBAL-H / toluene / 2 h / -78 °C 5: 96 percent / pyridine, DMAP / CH2Cl2 / 2 h / 0 °C 6: 1) hexamethyldisilazane (HMDS), ammonium sulfate, 2) trimethylsilyl triflate (TMSOTf) / 1) reflux, 1 h, 2) 1,2-dichloroethane, a) -22 deg C, 15 min, b) room temperature, 0.5 h 7: 90 percent / mercaptoethanol, sodium methoxide / methanol / 4 h / Heating 8: 90 percent / n-Bu3SnH, Et3B / benzene; hexane / Ambient temperature 9: 79 percent / TBAF / tetrahydrofuran / Ambient temperature View Scheme

1: 1) hexamethyldisilazane (HMDS), ammonium sulfate, 2) trimethylsilyl triflate (TMSOTf) / 1) reflux, 1 h, 2) 1,2-dichloroethane, a) -22 deg C, 15 min, b) room temperature, 0.5 h 2: 90 percent / mercaptoethanol, sodium methoxide / methanol / 4 h / Heating 3: 90 percent / n-Bu3SnH, Et3B / benzene; hexane / Ambient temperature 4: 79 percent / TBAF / tetrahydrofuran / Ambient temperature View Scheme

1: 1) lithium hexamethyldisilazide / 1) THF, -78 deg C, 1h, 2) room temperature, 30 min 2: tetrahydrofuran / -78 °C 3: DIBAL-H / toluene / 2 h / -78 °C 4: 96 percent / pyridine, DMAP / CH2Cl2 / 2 h / 0 °C 5: 1) hexamethyldisilazane (HMDS), ammonium sulfate, 2) trimethylsilyl triflate (TMSOTf) / 1) reflux, 1 h, 2) 1,2-dichloroethane, a) -22 deg C, 15 min, b) room temperature, 0.5 h 6: 90 percent / mercaptoethanol, sodium methoxide / methanol / 4 h / Heating 7: 90 percent / n-Bu3SnH, Et3B / benzene; hexane / Ambient temperature 8: 79 percent / TBAF / tetrahydrofuran / Ambient temperature View Scheme

1: tetrahydrofuran / -78 °C 2: DIBAL-H / toluene / 2 h / -78 °C 3: 96 percent / pyridine, DMAP / CH2Cl2 / 2 h / 0 °C 4: 1) hexamethyldisilazane (HMDS), ammonium sulfate, 2) trimethylsilyl triflate (TMSOTf) / 1) reflux, 1 h, 2) 1,2-dichloroethane, a) -22 deg C, 15 min, b) room temperature, 0.5 h 5: 90 percent / mercaptoethanol, sodium methoxide / methanol / 4 h / Heating 6: 90 percent / n-Bu3SnH, Et3B / benzene; hexane / Ambient temperature 7: 79 percent / TBAF / tetrahydrofuran / Ambient temperature View Scheme

1: DIBAL-H / toluene / 2 h / -78 °C 2: 96 percent / pyridine, DMAP / CH2Cl2 / 2 h / 0 °C 3: 1) hexamethyldisilazane (HMDS), ammonium sulfate, 2) trimethylsilyl triflate (TMSOTf) / 1) reflux, 1 h, 2) 1,2-dichloroethane, a) -22 deg C, 15 min, b) room temperature, 0.5 h 4: 90 percent / mercaptoethanol, sodium methoxide / methanol / 4 h / Heating 5: 90 percent / n-Bu3SnH, Et3B / benzene; hexane / Ambient temperature 6: 79 percent / TBAF / tetrahydrofuran / Ambient temperature View Scheme

1: 90 percent / mercaptoethanol, sodium methoxide / methanol / 4 h / Heating 2: 90 percent / n-Bu3SnH, Et3B / benzene; hexane / Ambient temperature 3: 79 percent / TBAF / tetrahydrofuran / Ambient temperature View Scheme

1: 90 percent / n-Bu3SnH, Et3B / benzene; hexane / Ambient temperature 2: 79 percent / TBAF / tetrahydrofuran / Ambient temperature View Scheme

1: dimethylformamide / 20 h / 20 °C 2: 61 percent / n-Bu3SnH; AIBN / toluene / 5 h / Heating 3: 94 percent / TBAF / tetrahydrofuran / 2 h / 20 °C View Scheme