1: 99 percent / triethylamine / dimethylformamide / 20 h / 25 °C 2: 1.) ozone, 2.) NaBH4 / 1.) EtOH, -78 deg C, 2.) aq. EtOH, 25 deg C, 10 h 3: tri-n-butylphosphine / CH2Cl2 / 2 h / 25 °C 4: m-chloroperbenzoic acid (MCPBA) / CH2Cl2 / 1.) 0 deg C, 10 min, 2.) 25 deg C, 2 h 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: 6.34 g / methyltriphenoxyphosphonium iodide / dimethylformamide / 0.25 h / 25 °C 2: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 30 min, 2.) -50 deg C, 10 h 3: 84 percent / LiAlH4 / tetrahydrofuran / 1.) -78 deg C, 10 min, 2.) 0 deg C, 60 min 4: oxalyl chloride, DMSO / CH2Cl2 / 0.5 h / -78 °C / 1.) CH2Cl2, -78 deg C, 30 min, 2.) -78 deg C, 15 min 5: CH2Cl2 / 12 h / 25 °C 6: 97 percent / 48percent aq. HF / acetonitrile / 1 h / 25 °C 7: H2, norbornadiene<1,4-bis(diphenylphosphino)butane>rhodium(I) tetrafluoroborate / CH2Cl2 / 12 h / 760 Torr 8: 92 percent / triethylamine, pyridine*SO3 / dimethylsulfoxide / 0.67 h / 25 °C 9: 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 10: 72 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 11: 84 percent / 40percent aq. HF / acetonitrile / 1 h / 25 °C 12: 1 N aq. LiOH / 1,2-dimethoxy-ethane / 0.75 h / 25 °C View Scheme

1: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 30 min, 2.) -50 deg C, 10 h 2: 84 percent / LiAlH4 / tetrahydrofuran / 1.) -78 deg C, 10 min, 2.) 0 deg C, 60 min 3: oxalyl chloride, DMSO / CH2Cl2 / 0.5 h / -78 °C / 1.) CH2Cl2, -78 deg C, 30 min, 2.) -78 deg C, 15 min 4: CH2Cl2 / 12 h / 25 °C 5: 97 percent / 48percent aq. HF / acetonitrile / 1 h / 25 °C 6: H2, norbornadiene<1,4-bis(diphenylphosphino)butane>rhodium(I) tetrafluoroborate / CH2Cl2 / 12 h / 760 Torr 7: 92 percent / triethylamine, pyridine*SO3 / dimethylsulfoxide / 0.67 h / 25 °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 / 1.) CH2Cl2, -78 deg C, 30 min, 2.) -78 deg C, 15 min 2: CH2Cl2 / 12 h / 25 °C 3: 97 percent / 48percent aq. HF / acetonitrile / 1 h / 25 °C 4: H2, norbornadiene<1,4-bis(diphenylphosphino)butane>rhodium(I) tetrafluoroborate / CH2Cl2 / 12 h / 760 Torr 5: 92 percent / triethylamine, pyridine*SO3 / dimethylsulfoxide / 0.67 h / 25 °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: H2, norbornadiene<1,4-bis(diphenylphosphino)butane>rhodium(I) tetrafluoroborate / CH2Cl2 / 12 h / 760 Torr 2: 92 percent / triethylamine, pyridine*SO3 / dimethylsulfoxide / 0.67 h / 25 °C 3: 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 4: 72 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 5: 84 percent / 40percent aq. HF / acetonitrile / 1 h / 25 °C 6: 1 N aq. LiOH / 1,2-dimethoxy-ethane / 0.75 h / 25 °C View Scheme

1: 95 percent / LiAlH4 / diethyl ether / 1.5 h / 25 °C 2: 99 percent / triethylamine / dimethylformamide / 20 h / 25 °C 3: 1.) ozone, 2.) NaBH4 / 1.) EtOH, -78 deg C, 2.) aq. EtOH, 25 deg C, 10 h 4: tri-n-butylphosphine / CH2Cl2 / 2 h / 25 °C 5: m-chloroperbenzoic acid (MCPBA) / CH2Cl2 / 1.) 0 deg C, 10 min, 2.) 25 deg C, 2 h 6: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min, 2.) -78 deg C, 1 h 7: tetrahydrofuran; hexane / 1.5 h / 25 °C 8: sodium amalgam / methanol; ethyl acetate / 20 h / -30 °C 9: 94 percent / Bu4NF / tetrahydrofuran / 21 h / 25 °C 10: oxalyl chloride, DMSO / CH2Cl2 / 0.42 h / -60 °C 11: 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 12: 72 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 13: 84 percent / 40percent aq. HF / acetonitrile / 1 h / 25 °C 14: 1 N aq. LiOH / 1,2-dimethoxy-ethane / 0.75 h / 25 °C View Scheme

1: 98 percent / diisobutylaluminum hydride (DIBAH) / CH2Cl2 / 1.) -78 deg C, 30 min, 2.) 0 deg C, 30 min 2: 6.34 g / methyltriphenoxyphosphonium iodide / dimethylformamide / 0.25 h / 25 °C 3: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 30 min, 2.) -50 deg C, 10 h 4: 84 percent / LiAlH4 / tetrahydrofuran / 1.) -78 deg C, 10 min, 2.) 0 deg C, 60 min 5: oxalyl chloride, DMSO / CH2Cl2 / 0.5 h / -78 °C / 1.) CH2Cl2, -78 deg C, 30 min, 2.) -78 deg C, 15 min 6: CH2Cl2 / 12 h / 25 °C 7: 97 percent / 48percent aq. HF / acetonitrile / 1 h / 25 °C 8: H2, norbornadiene<1,4-bis(diphenylphosphino)butane>rhodium(I) tetrafluoroborate / CH2Cl2 / 12 h / 760 Torr 9: 92 percent / triethylamine, pyridine*SO3 / dimethylsulfoxide / 0.67 h / 25 °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: 93 percent / diisobutylaluminum hydride (DIBAH) / CH2Cl2 / 1.) -78 deg C, 30 min, 2.) 0 deg C, 30 min 2: oxalyl chloride, DMSO / CH2Cl2 / 0.5 h / -78 °C 3: toluene / 12 h / 70 °C 4: 98 percent / diisobutylaluminum hydride (DIBAH) / CH2Cl2 / 1.) -78 deg C, 30 min, 2.) 0 deg C, 30 min 5: 6.34 g / methyltriphenoxyphosphonium iodide / dimethylformamide / 0.25 h / 25 °C 6: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 30 min, 2.) -50 deg C, 10 h 7: 84 percent / LiAlH4 / tetrahydrofuran / 1.) -78 deg C, 10 min, 2.) 0 deg C, 60 min 8: oxalyl chloride, DMSO / CH2Cl2 / 0.5 h / -78 °C / 1.) CH2Cl2, -78 deg C, 30 min, 2.) -78 deg C, 15 min 9: CH2Cl2 / 12 h / 25 °C 10: 97 percent / 48percent aq. HF / acetonitrile / 1 h / 25 °C 11: H2, norbornadiene<1,4-bis(diphenylphosphino)butane>rhodium(I) tetrafluoroborate / CH2Cl2 / 12 h / 760 Torr 12: 92 percent / triethylamine, pyridine*SO3 / dimethylsulfoxide / 0.67 h / 25 °C 13: 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 14: 72 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 15: 84 percent / 40percent aq. HF / acetonitrile / 1 h / 25 °C 16: 1 N aq. LiOH / 1,2-dimethoxy-ethane / 0.75 h / 25 °C View Scheme

1: 97 percent / 48percent aq. HF / acetonitrile / 1 h / 25 °C 2: H2, norbornadiene<1,4-bis(diphenylphosphino)butane>rhodium(I) tetrafluoroborate / CH2Cl2 / 12 h / 760 Torr 3: 92 percent / triethylamine, pyridine*SO3 / dimethylsulfoxide / 0.67 h / 25 °C 4: 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 5: 72 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 6: 84 percent / 40percent aq. HF / acetonitrile / 1 h / 25 °C 7: 1 N aq. LiOH / 1,2-dimethoxy-ethane / 0.75 h / 25 °C View Scheme

1: 91 percent / 1 N aq. HCl / 8 h / Heating 2: 95 percent / LiAlH4 / diethyl ether / 1.5 h / 25 °C 3: 99 percent / triethylamine / dimethylformamide / 20 h / 25 °C 4: 1.) ozone, 2.) NaBH4 / 1.) EtOH, -78 deg C, 2.) aq. EtOH, 25 deg C, 10 h 5: tri-n-butylphosphine / CH2Cl2 / 2 h / 25 °C 6: m-chloroperbenzoic acid (MCPBA) / CH2Cl2 / 1.) 0 deg C, 10 min, 2.) 25 deg C, 2 h 7: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, 30 min, 2.) -78 deg C, 1 h 8: tetrahydrofuran; hexane / 1.5 h / 25 °C 9: sodium amalgam / methanol; ethyl acetate / 20 h / -30 °C 10: 94 percent / Bu4NF / tetrahydrofuran / 21 h / 25 °C 11: oxalyl chloride, DMSO / CH2Cl2 / 0.42 h / -60 °C 12: 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 13: 72 percent / pyridine, CrO3 / CH2Cl2 / 0.25 h 14: 84 percent / 40percent aq. HF / acetonitrile / 1 h / 25 °C 15: 1 N aq. LiOH / 1,2-dimethoxy-ethane / 0.75 h / 25 °C View Scheme