lithium hydroxide in ethylene glycol dimethyl ether T=25°C; 0.75 h;

1: 2.01 g / triethylamine, 4-(dimethylamino)pyridine / CH2Cl2 / 12 h / 25 °C 2: 2.13 g / 2,2-dimethoxypropane, d,l-camphorsulfonic acid / 2 h / 25 °C 3: 1 N Bu4NF / tetrahydrofuran / 10 h / 25 °C 4: 95 percent / triethylamine, SO3*pyridine / dimethylsulfoxide / 0.75 h / 25 °C 5: 1.) sodium bis(trimethylsilyl)amide / 1.) toluene, 20 deg C, 15 min, 2a.) -78 deg C, 15 min, 2b.) 20 deg C, 30 min 6: 94 percent / Bu4NF / tetrahydrofuran / 36 h / 80 °C 7: 1.) mercuric acetate, 2.) NaBH4, 15percent aq. NaOH / 1.) CH2Cl2, 20 deg C, 7 h, 2.) MeOH, 20 deg C, 30 min 8: 100 percent / triethylamine / CH2Cl2 / 1.5 h / 0 °C 9: 94 percent / H2 / 10percent Pd/C / acetone / 3 h / 20 °C / 760 Torr 10: oxalyl chloride, DMSO / CH2Cl2 / 0.5 h / -78 °C 11: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min, 2.) -78 deg C, 1 h 12: tetrahydrofuran; hexane / 1.5 h / 25 °C 13: sodium amalgam / methanol; ethyl acetate / 20 h / -30 °C 14: 94 percent / Bu4NF / tetrahydrofuran / 21 h / 25 °C 15: oxalyl chloride, DMSO / CH2Cl2 / 0.42 h / -60 °C 16: 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 17: 72 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 18: 84 percent / 40percent aq. HF / acetonitrile / 1 h / 25 °C 19: 1 N aq. LiOH / 1,2-dimethoxy-ethane / 0.75 h / 25 °C View Scheme

1: 0.908 g / pyridine / 18 h / 5 °C 2: 0.468 g / lithium triethylborohydride / tetrahydrofuran / 24 h / 25 °C 3: 1.30 g / N-methylmorpholine N-oxide monohydrate, 0.16 M aq. osmium tetraoxide / acetone / 10 h / 25 °C 4: 2.01 g / triethylamine, 4-(dimethylamino)pyridine / CH2Cl2 / 12 h / 25 °C 5: 2.13 g / 2,2-dimethoxypropane, d,l-camphorsulfonic acid / 2 h / 25 °C 6: 1 N Bu4NF / tetrahydrofuran / 10 h / 25 °C 7: 95 percent / triethylamine, SO3*pyridine / dimethylsulfoxide / 0.75 h / 25 °C 8: 1.) sodium bis(trimethylsilyl)amide / 1.) toluene, 20 deg C, 15 min, 2a.) -78 deg C, 15 min, 2b.) 20 deg C, 30 min 9: 94 percent / Bu4NF / tetrahydrofuran / 36 h / 80 °C 10: 1.) mercuric acetate, 2.) NaBH4, 15percent aq. NaOH / 1.) CH2Cl2, 20 deg C, 7 h, 2.) MeOH, 20 deg C, 30 min 11: 100 percent / triethylamine / CH2Cl2 / 1.5 h / 0 °C 12: 94 percent / H2 / 10percent Pd/C / acetone / 3 h / 20 °C / 760 Torr 13: oxalyl chloride, DMSO / CH2Cl2 / 0.5 h / -78 °C 14: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min, 2.) -78 deg C, 1 h 15: tetrahydrofuran; hexane / 1.5 h / 25 °C 16: sodium amalgam / methanol; ethyl acetate / 20 h / -30 °C 17: 94 percent / Bu4NF / tetrahydrofuran / 21 h / 25 °C 18: oxalyl chloride, DMSO / CH2Cl2 / 0.42 h / -60 °C 19: 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 20: 72 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 21: 84 percent / 40percent aq. HF / acetonitrile / 1 h / 25 °C 22: 1 N aq. LiOH / 1,2-dimethoxy-ethane / 0.75 h / 25 °C View Scheme

1: 1.) ozone, 2.) dimethyl sulfide / 1.) CH2Cl2, -78 deg C, 2a.) -78 deg C, 1 h, 2b.) 20 deg C, 1 h 2: 55 percent / CH2Cl2; diethyl ether / 1.) -78 deg C, 8 h, 2.) 20 deg C, 2 h 3: 94 percent / triethylamine / CH2Cl2 / 2 h / 0 °C 4: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 19 h / 20 °C / 3040 Torr 5: 1.88 g / triethylamine / CH2Cl2 / 3 h / 0 °C 6: 1.84 g / NaI, NaHCO3, diisopropylethylamine / acetone / 18 h / 20 °C 7: 78 percent / diisopropylethylamine / toluene; acetonitrile / 54 h / 75 °C 8: 1.) sodium bis(trimethylsilyl)amide / 1.) toluene, 20 deg C, 15 min, 2a.) -78 deg C, 15 min, 2b.) 20 deg C, 30 min 9: 94 percent / Bu4NF / tetrahydrofuran / 36 h / 80 °C 10: 1.) mercuric acetate, 2.) NaBH4, 15percent aq. NaOH / 1.) CH2Cl2, 20 deg C, 7 h, 2.) MeOH, 20 deg C, 30 min 11: 100 percent / triethylamine / CH2Cl2 / 1.5 h / 0 °C 12: 94 percent / H2 / 10percent Pd/C / acetone / 3 h / 20 °C / 760 Torr 13: oxalyl chloride, DMSO / CH2Cl2 / 0.5 h / -78 °C 14: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min, 2.) -78 deg C, 1 h 15: tetrahydrofuran; hexane / 1.5 h / 25 °C 16: sodium amalgam / methanol; ethyl acetate / 20 h / -30 °C 17: 94 percent / Bu4NF / tetrahydrofuran / 21 h / 25 °C 18: oxalyl chloride, DMSO / CH2Cl2 / 0.42 h / -60 °C 19: 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 20: 72 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 21: 84 percent / 40percent aq. HF / acetonitrile / 1 h / 25 °C 22: 1 N aq. LiOH / 1,2-dimethoxy-ethane / 0.75 h / 25 °C View Scheme

1: 55 percent / CH2Cl2; diethyl ether / 1.) -78 deg C, 8 h, 2.) 20 deg C, 2 h 2: 94 percent / triethylamine / CH2Cl2 / 2 h / 0 °C 3: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 19 h / 20 °C / 3040 Torr 4: 1.88 g / triethylamine / CH2Cl2 / 3 h / 0 °C 5: 1.84 g / NaI, NaHCO3, diisopropylethylamine / acetone / 18 h / 20 °C 6: 78 percent / diisopropylethylamine / toluene; acetonitrile / 54 h / 75 °C 7: 1.) sodium bis(trimethylsilyl)amide / 1.) toluene, 20 deg C, 15 min, 2a.) -78 deg C, 15 min, 2b.) 20 deg C, 30 min 8: 94 percent / Bu4NF / tetrahydrofuran / 36 h / 80 °C 9: 1.) mercuric acetate, 2.) NaBH4, 15percent aq. NaOH / 1.) CH2Cl2, 20 deg C, 7 h, 2.) MeOH, 20 deg C, 30 min 10: 100 percent / triethylamine / CH2Cl2 / 1.5 h / 0 °C 11: 94 percent / H2 / 10percent Pd/C / acetone / 3 h / 20 °C / 760 Torr 12: oxalyl chloride, DMSO / CH2Cl2 / 0.5 h / -78 °C 13: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min, 2.) -78 deg C, 1 h 14: tetrahydrofuran; hexane / 1.5 h / 25 °C 15: sodium amalgam / methanol; ethyl acetate / 20 h / -30 °C 16: 94 percent / Bu4NF / tetrahydrofuran / 21 h / 25 °C 17: oxalyl chloride, DMSO / CH2Cl2 / 0.42 h / -60 °C 18: 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 19: 72 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 20: 84 percent / 40percent aq. HF / acetonitrile / 1 h / 25 °C 21: 1 N aq. LiOH / 1,2-dimethoxy-ethane / 0.75 h / 25 °C View Scheme

1: 0.468 g / lithium triethylborohydride / tetrahydrofuran / 24 h / 25 °C 2: 1.30 g / N-methylmorpholine N-oxide monohydrate, 0.16 M aq. osmium tetraoxide / acetone / 10 h / 25 °C 3: 2.01 g / triethylamine, 4-(dimethylamino)pyridine / CH2Cl2 / 12 h / 25 °C 4: 2.13 g / 2,2-dimethoxypropane, d,l-camphorsulfonic acid / 2 h / 25 °C 5: 1 N Bu4NF / tetrahydrofuran / 10 h / 25 °C 6: 95 percent / triethylamine, SO3*pyridine / dimethylsulfoxide / 0.75 h / 25 °C 7: 1.) sodium bis(trimethylsilyl)amide / 1.) toluene, 20 deg C, 15 min, 2a.) -78 deg C, 15 min, 2b.) 20 deg C, 30 min 8: 94 percent / Bu4NF / tetrahydrofuran / 36 h / 80 °C 9: 1.) mercuric acetate, 2.) NaBH4, 15percent aq. NaOH / 1.) CH2Cl2, 20 deg C, 7 h, 2.) MeOH, 20 deg C, 30 min 10: 100 percent / triethylamine / CH2Cl2 / 1.5 h / 0 °C 11: 94 percent / H2 / 10percent Pd/C / acetone / 3 h / 20 °C / 760 Torr 12: oxalyl chloride, DMSO / CH2Cl2 / 0.5 h / -78 °C 13: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min, 2.) -78 deg C, 1 h 14: tetrahydrofuran; hexane / 1.5 h / 25 °C 15: sodium amalgam / methanol; ethyl acetate / 20 h / -30 °C 16: 94 percent / Bu4NF / tetrahydrofuran / 21 h / 25 °C 17: oxalyl chloride, DMSO / CH2Cl2 / 0.42 h / -60 °C 18: 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 19: 72 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 20: 84 percent / 40percent aq. HF / acetonitrile / 1 h / 25 °C 21: 1 N aq. LiOH / 1,2-dimethoxy-ethane / 0.75 h / 25 °C View Scheme

1: 1.84 g / NaI, NaHCO3, diisopropylethylamine / acetone / 18 h / 20 °C 2: 78 percent / diisopropylethylamine / toluene; acetonitrile / 54 h / 75 °C 3: 1.) sodium bis(trimethylsilyl)amide / 1.) toluene, 20 deg C, 15 min, 2a.) -78 deg C, 15 min, 2b.) 20 deg C, 30 min 4: 94 percent / Bu4NF / tetrahydrofuran / 36 h / 80 °C 5: 1.) mercuric acetate, 2.) NaBH4, 15percent aq. NaOH / 1.) CH2Cl2, 20 deg C, 7 h, 2.) MeOH, 20 deg C, 30 min 6: 100 percent / triethylamine / CH2Cl2 / 1.5 h / 0 °C 7: 94 percent / H2 / 10percent Pd/C / acetone / 3 h / 20 °C / 760 Torr 8: oxalyl chloride, DMSO / CH2Cl2 / 0.5 h / -78 °C 9: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min, 2.) -78 deg C, 1 h 10: tetrahydrofuran; hexane / 1.5 h / 25 °C 11: sodium amalgam / methanol; ethyl acetate / 20 h / -30 °C 12: 94 percent / Bu4NF / tetrahydrofuran / 21 h / 25 °C 13: oxalyl chloride, DMSO / CH2Cl2 / 0.42 h / -60 °C 14: 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 15: 72 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 16: 84 percent / 40percent aq. HF / acetonitrile / 1 h / 25 °C 17: 1 N aq. LiOH / 1,2-dimethoxy-ethane / 0.75 h / 25 °C View Scheme

1: 1.) mercuric acetate, 2.) NaBH4, 15percent aq. NaOH / 1.) CH2Cl2, 20 deg C, 7 h, 2.) MeOH, 20 deg C, 30 min 2: 100 percent / triethylamine / CH2Cl2 / 1.5 h / 0 °C 3: 94 percent / H2 / 10percent Pd/C / acetone / 3 h / 20 °C / 760 Torr 4: oxalyl chloride, DMSO / CH2Cl2 / 0.5 h / -78 °C 5: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min, 2.) -78 deg C, 1 h 6: tetrahydrofuran; hexane / 1.5 h / 25 °C 7: sodium amalgam / methanol; ethyl acetate / 20 h / -30 °C 8: 94 percent / Bu4NF / tetrahydrofuran / 21 h / 25 °C 9: oxalyl chloride, DMSO / CH2Cl2 / 0.42 h / -60 °C 10: 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 11: 72 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 12: 84 percent / 40percent aq. HF / acetonitrile / 1 h / 25 °C 13: 1 N aq. LiOH / 1,2-dimethoxy-ethane / 0.75 h / 25 °C View Scheme

1: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 19 h / 20 °C / 3040 Torr 2: 1.88 g / triethylamine / CH2Cl2 / 3 h / 0 °C 3: 1.84 g / NaI, NaHCO3, diisopropylethylamine / acetone / 18 h / 20 °C 4: 78 percent / diisopropylethylamine / toluene; acetonitrile / 54 h / 75 °C 5: 1.) sodium bis(trimethylsilyl)amide / 1.) toluene, 20 deg C, 15 min, 2a.) -78 deg C, 15 min, 2b.) 20 deg C, 30 min 6: 94 percent / Bu4NF / tetrahydrofuran / 36 h / 80 °C 7: 1.) mercuric acetate, 2.) NaBH4, 15percent aq. NaOH / 1.) CH2Cl2, 20 deg C, 7 h, 2.) MeOH, 20 deg C, 30 min 8: 100 percent / triethylamine / CH2Cl2 / 1.5 h / 0 °C 9: 94 percent / H2 / 10percent Pd/C / acetone / 3 h / 20 °C / 760 Torr 10: oxalyl chloride, DMSO / CH2Cl2 / 0.5 h / -78 °C 11: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min, 2.) -78 deg C, 1 h 12: tetrahydrofuran; hexane / 1.5 h / 25 °C 13: sodium amalgam / methanol; ethyl acetate / 20 h / -30 °C 14: 94 percent / Bu4NF / tetrahydrofuran / 21 h / 25 °C 15: oxalyl chloride, DMSO / CH2Cl2 / 0.42 h / -60 °C 16: 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 17: 72 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 18: 84 percent / 40percent aq. HF / acetonitrile / 1 h / 25 °C 19: 1 N aq. LiOH / 1,2-dimethoxy-ethane / 0.75 h / 25 °C View Scheme

1: 1.) tri-n-butylborane, glacial acetic acid, 2.) lithium borohydride / 1.) THF, 25 deg C, 1.5 h, 2a.) 0 deg C, 1.5 h, 2b.) 25 deg C, 30 min 2: 0.908 g / pyridine / 18 h / 5 °C 3: 0.468 g / lithium triethylborohydride / tetrahydrofuran / 24 h / 25 °C 4: 1.30 g / N-methylmorpholine N-oxide monohydrate, 0.16 M aq. osmium tetraoxide / acetone / 10 h / 25 °C 5: 2.01 g / triethylamine, 4-(dimethylamino)pyridine / CH2Cl2 / 12 h / 25 °C 6: 2.13 g / 2,2-dimethoxypropane, d,l-camphorsulfonic acid / 2 h / 25 °C 7: 1 N Bu4NF / tetrahydrofuran / 10 h / 25 °C 8: 95 percent / triethylamine, SO3*pyridine / dimethylsulfoxide / 0.75 h / 25 °C 9: 1.) sodium bis(trimethylsilyl)amide / 1.) toluene, 20 deg C, 15 min, 2a.) -78 deg C, 15 min, 2b.) 20 deg C, 30 min 10: 94 percent / Bu4NF / tetrahydrofuran / 36 h / 80 °C 11: 1.) mercuric acetate, 2.) NaBH4, 15percent aq. NaOH / 1.) CH2Cl2, 20 deg C, 7 h, 2.) MeOH, 20 deg C, 30 min 12: 100 percent / triethylamine / CH2Cl2 / 1.5 h / 0 °C 13: 94 percent / H2 / 10percent Pd/C / acetone / 3 h / 20 °C / 760 Torr 14: oxalyl chloride, DMSO / CH2Cl2 / 0.5 h / -78 °C 15: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min, 2.) -78 deg C, 1 h 16: tetrahydrofuran; hexane / 1.5 h / 25 °C 17: sodium amalgam / methanol; ethyl acetate / 20 h / -30 °C 18: 94 percent / Bu4NF / tetrahydrofuran / 21 h / 25 °C 19: oxalyl chloride, DMSO / CH2Cl2 / 0.42 h / -60 °C 20: 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 21: 72 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 22: 84 percent / 40percent aq. HF / acetonitrile / 1 h / 25 °C 23: 1 N aq. LiOH / 1,2-dimethoxy-ethane / 0.75 h / 25 °C View Scheme