1: triethylamine / tetrahydrofuran / 1 h / -20 °C 2: NaN3 / tetrahydrofuran; H2O / -10 - 20 °C 3: benzene / 2 h / Heating 4: triethylamine / CH2Cl2 / 4 h / Heating 5: 98 percent / H2 / Pd/C / methanol / 20 °C View Scheme

1: benzene / 2 h / Heating 2: triethylamine / CH2Cl2 / 4 h / Heating 3: 98 percent / H2 / Pd/C / methanol / 20 °C View Scheme

1: 13.5 g / conc. H2SO4 / CH2Cl2 / 20 h / -78 deg C to room temperature 2: 1.) LDA, I2, 2.) DBU / 1.) THF, -78 deg C, 1.5 h, 2.) 0 deg C, 1 h, room temperature, 48 h 3: 2.) 2,6-di-tert-butylphenol / 1.) toluene, -78 deg C, 2.) THF, -78 deg C to room temperature, 30 min 4: 75 percent / 1.) H2, 2.) HCl / 1.) Pd-C / 1.) AcOH, 50 deg C, 4 bar, 2.) MeOH 5: 95 percent / TFA / 16 h / Ambient temperature View Scheme

1: boron trifluoride etherate / CH2Cl2 / 0.67 h / Ambient temperature 2: methanol / 4 h / Ambient temperature 3: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -70 deg C, 40 min, 2.) CH2Cl2, from -70 deg C to -5 deg C, 2 h 4: 91 percent / benzene / 6.5 h / Heating 5: 97 percent / sodium borohydride, cerium(III) chloride heptahydrate / ethanol / 0.67 h 6: 95 percent / pyridine / Ambient temperature 7: 36 percent / KH2PO4, K2HPO4, water / acetone / 12 h / Ambient temperature; lipase PS "Amano" 8: 93 percent / HgCl2, CaCO3, water / acetonitrile / 7 h / Heating 9: benzene 10: benzene / 3 h / Heating 11: H2, AcOH / 10percent Pd/C / 18 h / 760 Torr / Ambient temperature 12: Et3N / tetrahydrofuran; benzene / 1 h / Ambient temperature 13: 91 percent / NaIO4, KMnO4, KH2PO4, K2HPO4 / H2O; acetone / 3 h / Ambient temperature 14: 80 percent / 4 N HCl in dioxane / 1 h / Ambient temperature View Scheme

1: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -70 deg C, 40 min, 2.) CH2Cl2, from -70 deg C to -5 deg C, 2 h 2: 91 percent / benzene / 6.5 h / Heating 3: 97 percent / sodium borohydride, cerium(III) chloride heptahydrate / ethanol / 0.67 h 4: 95 percent / pyridine / Ambient temperature 5: 36 percent / KH2PO4, K2HPO4, water / acetone / 12 h / Ambient temperature; lipase PS "Amano" 6: 93 percent / HgCl2, CaCO3, water / acetonitrile / 7 h / Heating 7: benzene 8: benzene / 3 h / Heating 9: H2, AcOH / 10percent Pd/C / 18 h / 760 Torr / Ambient temperature 10: Et3N / tetrahydrofuran; benzene / 1 h / Ambient temperature 11: 91 percent / NaIO4, KMnO4, KH2PO4, K2HPO4 / H2O; acetone / 3 h / Ambient temperature 12: 80 percent / 4 N HCl in dioxane / 1 h / Ambient temperature View Scheme

1: methanol / 4 h / Ambient temperature 2: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -70 deg C, 40 min, 2.) CH2Cl2, from -70 deg C to -5 deg C, 2 h 3: 91 percent / benzene / 6.5 h / Heating 4: 97 percent / sodium borohydride, cerium(III) chloride heptahydrate / ethanol / 0.67 h 5: 95 percent / pyridine / Ambient temperature 6: 36 percent / KH2PO4, K2HPO4, water / acetone / 12 h / Ambient temperature; lipase PS "Amano" 7: 93 percent / HgCl2, CaCO3, water / acetonitrile / 7 h / Heating 8: benzene 9: benzene / 3 h / Heating 10: H2, AcOH / 10percent Pd/C / 18 h / 760 Torr / Ambient temperature 11: Et3N / tetrahydrofuran; benzene / 1 h / Ambient temperature 12: 91 percent / NaIO4, KMnO4, KH2PO4, K2HPO4 / H2O; acetone / 3 h / Ambient temperature 13: 80 percent / 4 N HCl in dioxane / 1 h / Ambient temperature View Scheme

1: 91 percent / benzene / 6.5 h / Heating 2: 97 percent / sodium borohydride, cerium(III) chloride heptahydrate / ethanol / 0.67 h 3: 95 percent / pyridine / Ambient temperature 4: 36 percent / KH2PO4, K2HPO4, water / acetone / 12 h / Ambient temperature; lipase PS "Amano" 5: 93 percent / HgCl2, CaCO3, water / acetonitrile / 7 h / Heating 6: benzene 7: benzene / 3 h / Heating 8: H2, AcOH / 10percent Pd/C / 18 h / 760 Torr / Ambient temperature 9: Et3N / tetrahydrofuran; benzene / 1 h / Ambient temperature 10: 91 percent / NaIO4, KMnO4, KH2PO4, K2HPO4 / H2O; acetone / 3 h / Ambient temperature 11: 80 percent / 4 N HCl in dioxane / 1 h / Ambient temperature View Scheme

1: 97 percent / sodium borohydride, cerium(III) chloride heptahydrate / ethanol / 0.67 h 2: 95 percent / pyridine / Ambient temperature 3: 36 percent / KH2PO4, K2HPO4, water / acetone / 12 h / Ambient temperature; lipase PS "Amano" 4: 93 percent / HgCl2, CaCO3, water / acetonitrile / 7 h / Heating 5: benzene 6: benzene / 3 h / Heating 7: H2, AcOH / 10percent Pd/C / 18 h / 760 Torr / Ambient temperature 8: Et3N / tetrahydrofuran; benzene / 1 h / Ambient temperature 9: 91 percent / NaIO4, KMnO4, KH2PO4, K2HPO4 / H2O; acetone / 3 h / Ambient temperature 10: 80 percent / 4 N HCl in dioxane / 1 h / Ambient temperature View Scheme

1: 36 percent / KH2PO4, K2HPO4, water / acetone / 12 h / Ambient temperature; lipase PS "Amano" 2: 93 percent / HgCl2, CaCO3, water / acetonitrile / 7 h / Heating 3: benzene 4: benzene / 3 h / Heating 5: H2, AcOH / 10percent Pd/C / 18 h / 760 Torr / Ambient temperature 6: Et3N / tetrahydrofuran; benzene / 1 h / Ambient temperature 7: 91 percent / NaIO4, KMnO4, KH2PO4, K2HPO4 / H2O; acetone / 3 h / Ambient temperature 8: 80 percent / 4 N HCl in dioxane / 1 h / Ambient temperature View Scheme

1: benzene 2: benzene / 3 h / Heating 3: H2, AcOH / 10percent Pd/C / 18 h / 760 Torr / Ambient temperature 4: Et3N / tetrahydrofuran; benzene / 1 h / Ambient temperature 5: 91 percent / NaIO4, KMnO4, KH2PO4, K2HPO4 / H2O; acetone / 3 h / Ambient temperature 6: 80 percent / 4 N HCl in dioxane / 1 h / Ambient temperature View Scheme