1: 92 percent / N-chlorosuccinimide / CH2Cl2 / 1 h / Ambient temperature 2: 79 percent / Cl2 gas / 2-methyl-propan-2-ol / 8 h / Ambient temperature 3: 59.5 percent / BCl3 / CH2Cl2 / 20 h / Ambient temperature View Scheme

1: 71 percent / 4 h / 80 °C / 10 - 15 Torr 2: 89 percent / Et3N / ethyl acetate / 4 h / Heating 3: 100 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene (DBU) / tetrahydrofuran / 0.5 h / 0 °C 4: 1.) N-hydroxysuccinimide, N,N-dicyclohexylcarbodiimide (DCC) / 1.) THF, 15 min, 2.) RT, 3 days 5: 95 percent / sat NaHCO3 aq / 0.67 h / Heating 6: 25 percent / PCl5, CaCO3 / nitromethane / 0.67 h / Heating 7: 61 percent / aluminium amalgam / diethyl ether; H2O / 1 h / Heating 8: 1.) oxalyl chloride, 2.) 4N HCl / 1.) DMF, benzene, reflux, 3.5 min,then RT, 2.) acetone, RT, 5h 9: lithium hydroxyde monohydrate / H2O 10: 57 percent / lithium hydroxide monohydrate / H2O; acetone / 2 h 11: 84 percent / potassium dihydrogen phosphate, 1N LiOH, hog kidney acylase I / H2O / 24 h View Scheme

1: 89 percent / Et3N / ethyl acetate / 4 h / Heating 2: 100 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene (DBU) / tetrahydrofuran / 0.5 h / 0 °C 3: 1.) N-hydroxysuccinimide, N,N-dicyclohexylcarbodiimide (DCC) / 1.) THF, 15 min, 2.) RT, 3 days 4: 95 percent / sat NaHCO3 aq / 0.67 h / Heating 5: 25 percent / PCl5, CaCO3 / nitromethane / 0.67 h / Heating 6: 61 percent / aluminium amalgam / diethyl ether; H2O / 1 h / Heating 7: 1.) oxalyl chloride, 2.) 4N HCl / 1.) DMF, benzene, reflux, 3.5 min,then RT, 2.) acetone, RT, 5h 8: lithium hydroxyde monohydrate / H2O 9: 57 percent / lithium hydroxide monohydrate / H2O; acetone / 2 h 10: 84 percent / potassium dihydrogen phosphate, 1N LiOH, hog kidney acylase I / H2O / 24 h View Scheme

1: 100 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene (DBU) / tetrahydrofuran / 0.5 h / 0 °C 2: 1.) N-hydroxysuccinimide, N,N-dicyclohexylcarbodiimide (DCC) / 1.) THF, 15 min, 2.) RT, 3 days 3: 95 percent / sat NaHCO3 aq / 0.67 h / Heating 4: 25 percent / PCl5, CaCO3 / nitromethane / 0.67 h / Heating 5: 61 percent / aluminium amalgam / diethyl ether; H2O / 1 h / Heating 6: 1.) oxalyl chloride, 2.) 4N HCl / 1.) DMF, benzene, reflux, 3.5 min,then RT, 2.) acetone, RT, 5h 7: lithium hydroxyde monohydrate / H2O 8: 57 percent / lithium hydroxide monohydrate / H2O; acetone / 2 h 9: 84 percent / potassium dihydrogen phosphate, 1N LiOH, hog kidney acylase I / H2O / 24 h View Scheme

1: lithium hydroxyde monohydrate / H2O 2: 57 percent / lithium hydroxide monohydrate / H2O; acetone / 2 h 3: 84 percent / potassium dihydrogen phosphate, 1N LiOH, hog kidney acylase I / H2O / 24 h View Scheme

1: 1.) N-hydroxysuccinimide, N,N-dicyclohexylcarbodiimide (DCC) / 1.) THF, 15 min, 2.) RT, 3 days 2: 95 percent / sat NaHCO3 aq / 0.67 h / Heating 3: 25 percent / PCl5, CaCO3 / nitromethane / 0.67 h / Heating 4: 61 percent / aluminium amalgam / diethyl ether; H2O / 1 h / Heating 5: 1.) oxalyl chloride, 2.) 4N HCl / 1.) DMF, benzene, reflux, 3.5 min,then RT, 2.) acetone, RT, 5h 6: lithium hydroxyde monohydrate / H2O 7: 57 percent / lithium hydroxide monohydrate / H2O; acetone / 2 h 8: 84 percent / potassium dihydrogen phosphate, 1N LiOH, hog kidney acylase I / H2O / 24 h View Scheme

Streptomyces sviceus;

2: 57 percent / hog kidney acylase I View Scheme