1: 1.) nBuLi, 2.) BF3*Et2O / 1.) hexane, THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 h and -50 deg C, 1 h. 2: 71 percent / Na-Hg / methanol 3: N,N-diisopropylethylamine / CH2Cl2 / 0.5 h / 0 °C 4: pyridinium p-toluenesulfonate / methanol / 1.) room temperature, overnight, 2.) 50 deg C, 1 h. 5: 1.) 2,4,6-trichlorobenzoyl chloride, Et3N, 2.) 4-dimethylaminopyridine / 1.) toluene, room temperature, 2 h, 2.) toluene, room temperature, 30 min. 6: 1.) pyridinium poly(hydrogen fluoride), 2.) Hg(ClO4)2*3H2O, CaCO3 / 1.) THF, room temperature, overnight, 2.) acetonitrile, H2O, room temperature, 5 min. View Scheme

1: 1.) n-BuLi, 2.) TsCl / 1.) THF, 0 deg C, 10 min, 2.) THF, 0 deg C, 20 min. 2: 1.) nBuLi, 2.) BF3*Et2O / 1.) hexane, THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 h and -50 deg C, 1 h. 3: 71 percent / Na-Hg / methanol 4: N,N-diisopropylethylamine / CH2Cl2 / 0.5 h / 0 °C 5: pyridinium p-toluenesulfonate / methanol / 1.) room temperature, overnight, 2.) 50 deg C, 1 h. 6: 1.) 2,4,6-trichlorobenzoyl chloride, Et3N, 2.) 4-dimethylaminopyridine / 1.) toluene, room temperature, 2 h, 2.) toluene, room temperature, 30 min. 7: 1.) pyridinium poly(hydrogen fluoride), 2.) Hg(ClO4)2*3H2O, CaCO3 / 1.) THF, room temperature, overnight, 2.) acetonitrile, H2O, room temperature, 5 min. View Scheme

1: N,N-diisopropylethylamine / CH2Cl2 / 0.5 h / 0 °C 2: pyridinium p-toluenesulfonate / methanol / 1.) room temperature, overnight, 2.) 50 deg C, 1 h. 3: 1.) 2,4,6-trichlorobenzoyl chloride, Et3N, 2.) 4-dimethylaminopyridine / 1.) toluene, room temperature, 2 h, 2.) toluene, room temperature, 30 min. 4: 1.) pyridinium poly(hydrogen fluoride), 2.) Hg(ClO4)2*3H2O, CaCO3 / 1.) THF, room temperature, overnight, 2.) acetonitrile, H2O, room temperature, 5 min. View Scheme

1: N,N-diisopropylethylamine / CH2Cl2 / 0.25 h / 0 °C 2: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 0.5 h / Ambient temperature 3: 1.) 2,4,6-trichlorobenzoyl chloride, Et3N, 2.) 4-dimethylaminopyridine / 1.) toluene, room temperature, 2 h, 2.) toluene, overnight. 4: 31 percent / AgNO3, phosphate buffer, N-chlorosuccinimide / acetone / 0.17 h / Ambient temperature; pH=7 6: 80 percent / pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 0 °C View Scheme

1: 71 percent / Na-Hg / methanol 2: N,N-diisopropylethylamine / CH2Cl2 / 0.5 h / 0 °C 3: pyridinium p-toluenesulfonate / methanol / 1.) room temperature, overnight, 2.) 50 deg C, 1 h. 4: 1.) 2,4,6-trichlorobenzoyl chloride, Et3N, 2.) 4-dimethylaminopyridine / 1.) toluene, room temperature, 2 h, 2.) toluene, room temperature, 30 min. 5: 1.) pyridinium poly(hydrogen fluoride), 2.) Hg(ClO4)2*3H2O, CaCO3 / 1.) THF, room temperature, overnight, 2.) acetonitrile, H2O, room temperature, 5 min. View Scheme

1: 96 percent / NaHg / methanol 2: N,N-diisopropylethylamine / CH2Cl2 / 0.25 h / 0 °C 3: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 0.5 h / Ambient temperature 4: 1.) 2,4,6-trichlorobenzoyl chloride, Et3N, 2.) 4-dimethylaminopyridine / 1.) toluene, room temperature, 2 h, 2.) toluene, overnight. 5: 31 percent / AgNO3, phosphate buffer, N-chlorosuccinimide / acetone / 0.17 h / Ambient temperature; pH=7 7: 80 percent / pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 0 °C View Scheme

1: 31 percent / AgNO3, phosphate buffer, N-chlorosuccinimide / acetone / 0.17 h / Ambient temperature; pH=7 3: 80 percent / pyridinium poly(hydrogen fluoride) / tetrahydrofuran / 0 °C View Scheme

1: 97 percent / diethylphosphoryl cyanide, Et3N / dimethylformamide / 1 h / 0 - 20 °C 2: 1.) LDA / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 2 h 3: (S)-(-)-2-methyl-CBS-oxazaborolidine / tetrahydrofuran / 1 h / 0 °C 4: 99 percent / i-Pr2NEt / CH2Cl2 / 0.5 h / 0 °C 5: 100 percent / aq. LiOH / tetrahydrofuran / 48 h / Ambient temperature 6: Et3N / toluene / 2 h / Ambient temperature 7: DMAP / toluene / 12 h / 50 °C 8: 76 percent / DDQ / CH2Cl2; H2O / 1.5 h / Ambient temperature 9: 87 percent / TPAP, NMO, MS4A / acetonitrile / 1 h / Ambient temperature 10: 1.) NBS, 2.) CrO3, H2SO4 / 1.) THF, phosphate buffer pH 7, 0 deg C, 15 min, 2.) acetone, 0 deg C, 15 min 11: MS 4A, PPC / CH2Cl2 / 12 h / Ambient temperature 12: HF*pyridine / tetrahydrofuran / Ambient temperature View Scheme

1: Et3N / toluene / 2 h / Ambient temperature 2: DMAP / toluene / 12 h / 50 °C 3: 76 percent / DDQ / CH2Cl2; H2O / 1.5 h / Ambient temperature 4: 87 percent / TPAP, NMO, MS4A / acetonitrile / 1 h / Ambient temperature 5: 1.) NBS, 2.) CrO3, H2SO4 / 1.) THF, phosphate buffer pH 7, 0 deg C, 15 min, 2.) acetone, 0 deg C, 15 min 6: MS 4A, PPC / CH2Cl2 / 12 h / Ambient temperature 7: HF*pyridine / tetrahydrofuran / Ambient temperature View Scheme

1: 1.) LDA / 1.) THF, -78 deg C, 20 min, 2.) THF, -78 deg C, 2 h 2: (S)-(-)-2-methyl-CBS-oxazaborolidine / tetrahydrofuran / 1 h / 0 °C 3: 99 percent / i-Pr2NEt / CH2Cl2 / 0.5 h / 0 °C 4: 100 percent / aq. LiOH / tetrahydrofuran / 48 h / Ambient temperature 5: Et3N / toluene / 2 h / Ambient temperature 6: DMAP / toluene / 12 h / 50 °C 7: 76 percent / DDQ / CH2Cl2; H2O / 1.5 h / Ambient temperature 8: 87 percent / TPAP, NMO, MS4A / acetonitrile / 1 h / Ambient temperature 9: 1.) NBS, 2.) CrO3, H2SO4 / 1.) THF, phosphate buffer pH 7, 0 deg C, 15 min, 2.) acetone, 0 deg C, 15 min 10: MS 4A, PPC / CH2Cl2 / 12 h / Ambient temperature 11: HF*pyridine / tetrahydrofuran / Ambient temperature View Scheme