18 h; Ambient temperaturehydrolysis porcine liver esterase;

1: 1) t-butyllithium; 2) copper(I)iodide, tributylphosphine 2: 1) triphenylphosphine; 2) 25percent aq. TiCl3, NH4OAc / 1) THF, rt., 15 min; 2) THF-water-MeOH, rt., 5 h 3: 92 percent / hydrogen fluoride-pyridine / acetonitrile / 1.5 h / Ambient temperature 4: 89 percent / porcine liver esterase, phosphate buffer solution (pH=8) / acetone; H2O / 20 h / Ambient temperature View Scheme

1: 51 percent / sodium nitrite, phloroglucinol / dimethylsulfoxide / 20 h / Ambient temperature 2: 1) 3N sodium hydroxide; 3) acetic acid / 1) H2O, 0 deg C, 3 h; 2) H2O, 0 deg C, 5 h; 3) H2O, room temp., 20 h 3: 79 percent / mesyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C 4: 1) t-butyllithium; 2) copper(I)iodide, tributylphosphine 5: 1) triphenylphosphine; 2) 25percent aq. TiCl3, NH4OAc / 1) THF, rt., 15 min; 2) THF-water-MeOH, rt., 5 h 6: 92 percent / hydrogen fluoride-pyridine / acetonitrile / 1.5 h / Ambient temperature 7: 89 percent / porcine liver esterase, phosphate buffer solution (pH=8) / acetone; H2O / 20 h / Ambient temperature View Scheme

1: 1) triphenylphosphine; 2) 25percent aq. TiCl3, NH4OAc / 1) THF, rt., 15 min; 2) THF-water-MeOH, rt., 5 h 2: 92 percent / hydrogen fluoride-pyridine / acetonitrile / 1.5 h / Ambient temperature 3: 89 percent / porcine liver esterase, phosphate buffer solution (pH=8) / acetone; H2O / 20 h / Ambient temperature View Scheme

1: 1) 3N sodium hydroxide; 3) acetic acid / 1) H2O, 0 deg C, 3 h; 2) H2O, 0 deg C, 5 h; 3) H2O, room temp., 20 h 2: 79 percent / mesyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C 3: 1) t-butyllithium; 2) copper(I)iodide, tributylphosphine 4: 1) triphenylphosphine; 2) 25percent aq. TiCl3, NH4OAc / 1) THF, rt., 15 min; 2) THF-water-MeOH, rt., 5 h 5: 92 percent / hydrogen fluoride-pyridine / acetonitrile / 1.5 h / Ambient temperature 6: 89 percent / porcine liver esterase, phosphate buffer solution (pH=8) / acetone; H2O / 20 h / Ambient temperature View Scheme

1: potassium acetate 2: 92 percent / hydrogen fluoride-pyridine / acetonitrile / 1.5 h / Ambient temperature 3: 89 percent / porcine liver esterase, phosphate buffer solution (pH=8) / acetone; H2O / 20 h / Ambient temperature View Scheme

1: 92 percent / hydrogen fluoride-pyridine / acetonitrile / 1.5 h / Ambient temperature 2: 89 percent / porcine liver esterase, phosphate buffer solution (pH=8) / acetone; H2O / 20 h / Ambient temperature View Scheme

1: 79 percent / mesyl chloride, triethylamine / CH2Cl2 / 1 h / 0 °C 2: 1) t-butyllithium; 2) copper(I)iodide, tributylphosphine 3: 1) triphenylphosphine; 2) 25percent aq. TiCl3, NH4OAc / 1) THF, rt., 15 min; 2) THF-water-MeOH, rt., 5 h 4: 92 percent / hydrogen fluoride-pyridine / acetonitrile / 1.5 h / Ambient temperature 5: 89 percent / porcine liver esterase, phosphate buffer solution (pH=8) / acetone; H2O / 20 h / Ambient temperature View Scheme

1: 10 percent 2: on a silicagel TLC plate 3: 92 percent / hydrogenfluoride-pyridine / acetonitrile / 3 h / Ambient temperature 4: 89 percent / 18 h / Ambient temperature; hydrolysis porcine liver esterase View Scheme

1: 94 percent / 25percent aq.titanium(III)trichloride, ammonium acetate / tetrahydrofuran; H2O / 24 h / Ambient temperature 2: 92 percent / hydrogen fluoride-pyridine / acetonitrile / 1.5 h / Ambient temperature 3: 89 percent / porcine liver esterase, phosphate buffer solution (pH=8) / acetone; H2O / 20 h / Ambient temperature View Scheme