1: 92 percent / triethylamine, pyridine*SO3 / dimethylsulfoxide / 0.67 h / 25 °C 2: 1.) di-n-butylboryl triflate, diisopropylethylamine / 1.) CH2Cl2, -78 deg C, 30 min, 2a.) -78 deg C, 1 h, 2b.) 0 deg C, 1.5 h 3: 72 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 4: 84 percent / 40percent aq. HF / acetonitrile / 1 h / 25 °C 5: 1 N aq. LiOH / 1,2-dimethoxy-ethane / 0.75 h / 25 °C View Scheme

1: tri-n-butylphosphine / CH2Cl2 / 2 h / 25 °C 2: m-chloroperbenzoic acid (MCPBA) / CH2Cl2 / 1.) 0 deg C, 10 min, 2.) 25 deg C, 2 h 3: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min, 2.) -78 deg C, 1 h 4: tetrahydrofuran; hexane / 1.5 h / 25 °C 5: sodium amalgam / methanol; ethyl acetate / 20 h / -30 °C 6: 94 percent / Bu4NF / tetrahydrofuran / 21 h / 25 °C 7: oxalyl chloride, DMSO / CH2Cl2 / 0.42 h / -60 °C 8: 1.) di-n-butylboryl triflate, diisopropylethylamine / 1.) CH2Cl2, -78 deg C, 30 min, 2a.) -78 deg C, 1 h, 2b.) 0 deg C, 1.5 h 9: 72 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 10: 84 percent / 40percent aq. HF / acetonitrile / 1 h / 25 °C 11: 1 N aq. LiOH / 1,2-dimethoxy-ethane / 0.75 h / 25 °C View Scheme

1: oxalyl chloride, DMSO / CH2Cl2 / 0.5 h / -78 °C 2: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min, 2.) -78 deg C, 1 h 3: tetrahydrofuran; hexane / 1.5 h / 25 °C 4: sodium amalgam / methanol; ethyl acetate / 20 h / -30 °C 5: 94 percent / Bu4NF / tetrahydrofuran / 21 h / 25 °C 6: oxalyl chloride, DMSO / CH2Cl2 / 0.42 h / -60 °C 7: 1.) di-n-butylboryl triflate, diisopropylethylamine / 1.) CH2Cl2, -78 deg C, 30 min, 2a.) -78 deg C, 1 h, 2b.) 0 deg C, 1.5 h 8: 72 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 9: 84 percent / 40percent aq. HF / acetonitrile / 1 h / 25 °C 10: 1 N aq. LiOH / 1,2-dimethoxy-ethane / 0.75 h / 25 °C View Scheme

1: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min, 2.) -78 deg C, 1 h 2: tetrahydrofuran; hexane / 1.5 h / 25 °C 3: sodium amalgam / methanol; ethyl acetate / 20 h / -30 °C 4: 94 percent / Bu4NF / tetrahydrofuran / 21 h / 25 °C 5: oxalyl chloride, DMSO / CH2Cl2 / 0.42 h / -60 °C 6: 1.) di-n-butylboryl triflate, diisopropylethylamine / 1.) CH2Cl2, -78 deg C, 30 min, 2a.) -78 deg C, 1 h, 2b.) 0 deg C, 1.5 h 7: 72 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 8: 84 percent / 40percent aq. HF / acetonitrile / 1 h / 25 °C 9: 1 N aq. LiOH / 1,2-dimethoxy-ethane / 0.75 h / 25 °C View Scheme

1: oxalyl chloride, DMSO / CH2Cl2 / 0.42 h / -60 °C 2: 1.) di-n-butylboryl triflate, diisopropylethylamine / 1.) CH2Cl2, -78 deg C, 30 min, 2a.) -78 deg C, 1 h, 2b.) 0 deg C, 1.5 h 3: 72 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 4: 84 percent / 40percent aq. HF / acetonitrile / 1 h / 25 °C 5: 1 N aq. LiOH / 1,2-dimethoxy-ethane / 0.75 h / 25 °C View Scheme

1: 1.) di-n-butylboryl triflate, diisopropylethylamine / 1.) CH2Cl2, -78 deg C, 30 min, 2a.) -78 deg C, 1 h, 2b.) 0 deg C, 1.5 h 2: 72 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 3: 84 percent / 40percent aq. HF / acetonitrile / 1 h / 25 °C 4: 1 N aq. LiOH / 1,2-dimethoxy-ethane / 0.75 h / 25 °C View Scheme

1.1: 100 percent / NaBH4 / methanol / 0.75 h / 0 - 20 °C 2.1: 77 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 1 h / 0 - 20 °C 3.1: 95 percent / Mo7O24(NH4)6*4H2O; H2O2 / ethanol; H2O / 18 h / 20 °C 4.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h 4.2: 85 percent / tetrahydrofuran; toluene / -78 - 20 °C 5.1: 97 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H2O; CH2Cl2 / 2 h / 0 °C 6.1: DMSO; oxalyl chloride; Et3N / CH2Cl2 / 0.92 h / -78 °C 7.1: dibutylboron triflate; diisopropylethylamine / CH2Cl2 / 0.5 h / -78 °C 7.2: CH2Cl2 / 3 h / -78 - 20 °C 8.1: 12 mg / pyridine; chromium trioxide / CH2Cl2 / 0.33 h / 20 °C 9.1: 85 percent / HF / H2O; acetonitrile / 3 h / 20 °C 10.1: LiOH / H2O; 1,2-dimethoxy-ethane / 7 h / 80 °C View Scheme

1.1: 84 percent / DIBAL-H / CH2Cl2; toluene / 4 h / -78 °C 2.1: 100 percent / NaBH4 / methanol / 0.75 h / 0 - 20 °C 3.1: 77 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 1 h / 0 - 20 °C 4.1: 95 percent / Mo7O24(NH4)6*4H2O; H2O2 / ethanol; H2O / 18 h / 20 °C 5.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h 5.2: 85 percent / tetrahydrofuran; toluene / -78 - 20 °C 6.1: 97 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H2O; CH2Cl2 / 2 h / 0 °C 7.1: DMSO; oxalyl chloride; Et3N / CH2Cl2 / 0.92 h / -78 °C 8.1: dibutylboron triflate; diisopropylethylamine / CH2Cl2 / 0.5 h / -78 °C 8.2: CH2Cl2 / 3 h / -78 - 20 °C 9.1: 12 mg / pyridine; chromium trioxide / CH2Cl2 / 0.33 h / 20 °C 10.1: 85 percent / HF / H2O; acetonitrile / 3 h / 20 °C 11.1: LiOH / H2O; 1,2-dimethoxy-ethane / 7 h / 80 °C View Scheme

1.1: 77 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 1 h / 0 - 20 °C 2.1: 95 percent / Mo7O24(NH4)6*4H2O; H2O2 / ethanol; H2O / 18 h / 20 °C 3.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h 3.2: 85 percent / tetrahydrofuran; toluene / -78 - 20 °C 4.1: 97 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H2O; CH2Cl2 / 2 h / 0 °C 5.1: DMSO; oxalyl chloride; Et3N / CH2Cl2 / 0.92 h / -78 °C 6.1: dibutylboron triflate; diisopropylethylamine / CH2Cl2 / 0.5 h / -78 °C 6.2: CH2Cl2 / 3 h / -78 - 20 °C 7.1: 12 mg / pyridine; chromium trioxide / CH2Cl2 / 0.33 h / 20 °C 8.1: 85 percent / HF / H2O; acetonitrile / 3 h / 20 °C 9.1: LiOH / H2O; 1,2-dimethoxy-ethane / 7 h / 80 °C View Scheme

1.1: 95 percent / dimethylsulfoxide / 5 h / 85 °C 2.1: 84 percent / DIBAL-H / CH2Cl2; toluene / 4 h / -78 °C 3.1: 100 percent / NaBH4 / methanol / 0.75 h / 0 - 20 °C 4.1: 77 percent / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 1 h / 0 - 20 °C 5.1: 95 percent / Mo7O24(NH4)6*4H2O; H2O2 / ethanol; H2O / 18 h / 20 °C 6.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h 6.2: 85 percent / tetrahydrofuran; toluene / -78 - 20 °C 7.1: 97 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H2O; CH2Cl2 / 2 h / 0 °C 8.1: DMSO; oxalyl chloride; Et3N / CH2Cl2 / 0.92 h / -78 °C 9.1: dibutylboron triflate; diisopropylethylamine / CH2Cl2 / 0.5 h / -78 °C 9.2: CH2Cl2 / 3 h / -78 - 20 °C 10.1: 12 mg / pyridine; chromium trioxide / CH2Cl2 / 0.33 h / 20 °C 11.1: 85 percent / HF / H2O; acetonitrile / 3 h / 20 °C 12.1: LiOH / H2O; 1,2-dimethoxy-ethane / 7 h / 80 °C View Scheme