1: 97 percent / NaH, 18-crown-6 / tetrahydrofuran / 3 h 2: 1.) n-butyllithium / 1.) THF, hexane, -23 deg C, 80 min, 2.) THF, hexane, 5 min 3: 1.) KH, 2.) tetrabutylammonium chloride, 18-crown-6 / 1.) THF, 15 min, 2.) THF, RT, 20 min 4: 86 percent / sodium naphthalenide / 1,2-dimethoxy-ethane / 0.67 h / -78 °C 5: 99 percent / K2CO3 / tetrahydrofuran; toluene 6: 85 percent / MeI, H2O / acetonitrile / Ambient temperature 7: 1.) t-BuLi, 2.) dineopentylzinc 8: (CH3)2SO, pyridine, CF3COOH, dicyclohexylcarbodiimide (DCC) / benzene / 0.5 h / Ambient temperature 9: benzene; diethyl ether / 0.33 h 10: n-Bu4NF / tetrahydrofuran / 0.25 h / 0 °C 11: 75percent aq. CH3COOH / tetrahydrofuran / 0 - 5 °C 12: 68 percent / diethyl cyanophosphonate, Et3N / dimethylformamide / 0.5 h / 0 °C 13: 86 percent / (COCl)2, (CH3)2SO / CH2Cl2 / 0.33 h / -78 °C 14: 69 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 2.5 h / 0 °C 15: 100 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), H2O / CH2Cl2 / 0.5 h / Ambient temperature 16: 64 percent / CF3COOH / 2.5 h / Ambient temperature View Scheme

1: 83 percent / MnO2 / pentane / 60 h 2: 1.) n-BuLi / 1.) THF, hexane, from 20 deg C to 0 deg C, 10 min, 2.) THF, hexane, 0.5 h 3: 98 percent / toluene / 8 h / Heating 4: diisobutylaluminum hydride (DIBAL) / CH2Cl2; hexane / 0.5 h / -78 °C 5: 1 M aq. HCl / diethyl ether / 1 h 6: 1.) t-BuLi, 2.) dineopentylzinc 7: (CH3)2SO, pyridine, CF3COOH, dicyclohexylcarbodiimide (DCC) / benzene / 0.5 h / Ambient temperature 8: benzene; diethyl ether / 0.33 h 9: n-Bu4NF / tetrahydrofuran / 0.25 h / 0 °C 10: 75percent aq. CH3COOH / tetrahydrofuran / 0 - 5 °C 11: 68 percent / diethyl cyanophosphonate, Et3N / dimethylformamide / 0.5 h / 0 °C 12: 86 percent / (COCl)2, (CH3)2SO / CH2Cl2 / 0.33 h / -78 °C 13: 69 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 2.5 h / 0 °C 14: 100 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), H2O / CH2Cl2 / 0.5 h / Ambient temperature 15: 64 percent / CF3COOH / 2.5 h / Ambient temperature View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, from 20 deg C to 0 deg C, 10 min, 2.) THF, hexane, 0.5 h 2: 98 percent / toluene / 8 h / Heating 3: diisobutylaluminum hydride (DIBAL) / CH2Cl2; hexane / 0.5 h / -78 °C 4: 1 M aq. HCl / diethyl ether / 1 h 5: 1.) t-BuLi, 2.) dineopentylzinc 6: (CH3)2SO, pyridine, CF3COOH, dicyclohexylcarbodiimide (DCC) / benzene / 0.5 h / Ambient temperature 7: benzene; diethyl ether / 0.33 h 8: n-Bu4NF / tetrahydrofuran / 0.25 h / 0 °C 9: 75percent aq. CH3COOH / tetrahydrofuran / 0 - 5 °C 10: 68 percent / diethyl cyanophosphonate, Et3N / dimethylformamide / 0.5 h / 0 °C 11: 86 percent / (COCl)2, (CH3)2SO / CH2Cl2 / 0.33 h / -78 °C 12: 69 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 2.5 h / 0 °C 13: 100 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), H2O / CH2Cl2 / 0.5 h / Ambient temperature 14: 64 percent / CF3COOH / 2.5 h / Ambient temperature View Scheme

1: diisobutylaluminum hydride (DIBAL) / CH2Cl2; hexane / 0.5 h / -78 °C 2: 1 M aq. HCl / diethyl ether / 1 h 3: 1.) t-BuLi, 2.) dineopentylzinc 4: (CH3)2SO, pyridine, CF3COOH, dicyclohexylcarbodiimide (DCC) / benzene / 0.5 h / Ambient temperature 5: benzene; diethyl ether / 0.33 h 6: n-Bu4NF / tetrahydrofuran / 0.25 h / 0 °C 7: 75percent aq. CH3COOH / tetrahydrofuran / 0 - 5 °C 8: 68 percent / diethyl cyanophosphonate, Et3N / dimethylformamide / 0.5 h / 0 °C 9: 86 percent / (COCl)2, (CH3)2SO / CH2Cl2 / 0.33 h / -78 °C 10: 69 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 2.5 h / 0 °C 11: 100 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), H2O / CH2Cl2 / 0.5 h / Ambient temperature 12: 64 percent / CF3COOH / 2.5 h / Ambient temperature View Scheme

1: 98 percent / toluene / 8 h / Heating 2: diisobutylaluminum hydride (DIBAL) / CH2Cl2; hexane / 0.5 h / -78 °C 3: 1 M aq. HCl / diethyl ether / 1 h 4: 1.) t-BuLi, 2.) dineopentylzinc 5: (CH3)2SO, pyridine, CF3COOH, dicyclohexylcarbodiimide (DCC) / benzene / 0.5 h / Ambient temperature 6: benzene; diethyl ether / 0.33 h 7: n-Bu4NF / tetrahydrofuran / 0.25 h / 0 °C 8: 75percent aq. CH3COOH / tetrahydrofuran / 0 - 5 °C 9: 68 percent / diethyl cyanophosphonate, Et3N / dimethylformamide / 0.5 h / 0 °C 10: 86 percent / (COCl)2, (CH3)2SO / CH2Cl2 / 0.33 h / -78 °C 11: 69 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 2.5 h / 0 °C 12: 100 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), H2O / CH2Cl2 / 0.5 h / Ambient temperature 13: 64 percent / CF3COOH / 2.5 h / Ambient temperature View Scheme

1: 80 percent / pyridine / 48 h / Ambient temperature 2: 97 percent / NaH, 18-crown-6 / tetrahydrofuran / 3 h 3: 1.) n-butyllithium / 1.) THF, hexane, -23 deg C, 80 min, 2.) THF, hexane, 5 min 4: 1.) KH, 2.) tetrabutylammonium chloride, 18-crown-6 / 1.) THF, 15 min, 2.) THF, RT, 20 min 5: 86 percent / sodium naphthalenide / 1,2-dimethoxy-ethane / 0.67 h / -78 °C 6: 99 percent / K2CO3 / tetrahydrofuran; toluene 7: 85 percent / MeI, H2O / acetonitrile / Ambient temperature 8: 1.) t-BuLi, 2.) dineopentylzinc 9: (CH3)2SO, pyridine, CF3COOH, dicyclohexylcarbodiimide (DCC) / benzene / 0.5 h / Ambient temperature 10: benzene; diethyl ether / 0.33 h 11: n-Bu4NF / tetrahydrofuran / 0.25 h / 0 °C 12: 75percent aq. CH3COOH / tetrahydrofuran / 0 - 5 °C 13: 68 percent / diethyl cyanophosphonate, Et3N / dimethylformamide / 0.5 h / 0 °C 14: 86 percent / (COCl)2, (CH3)2SO / CH2Cl2 / 0.33 h / -78 °C 15: 69 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 2.5 h / 0 °C 16: 100 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), H2O / CH2Cl2 / 0.5 h / Ambient temperature 17: 64 percent / CF3COOH / 2.5 h / Ambient temperature View Scheme

1: 96 percent / CH3COOH, H2O / tetrahydrofuran / 1 h / Ambient temperature 2: 80 percent / pyridine / 48 h / Ambient temperature 3: 97 percent / NaH, 18-crown-6 / tetrahydrofuran / 3 h 4: 1.) n-butyllithium / 1.) THF, hexane, -23 deg C, 80 min, 2.) THF, hexane, 5 min 5: 1.) KH, 2.) tetrabutylammonium chloride, 18-crown-6 / 1.) THF, 15 min, 2.) THF, RT, 20 min 6: 86 percent / sodium naphthalenide / 1,2-dimethoxy-ethane / 0.67 h / -78 °C 7: 99 percent / K2CO3 / tetrahydrofuran; toluene 8: 85 percent / MeI, H2O / acetonitrile / Ambient temperature 9: 1.) t-BuLi, 2.) dineopentylzinc 10: (CH3)2SO, pyridine, CF3COOH, dicyclohexylcarbodiimide (DCC) / benzene / 0.5 h / Ambient temperature 11: benzene; diethyl ether / 0.33 h 12: n-Bu4NF / tetrahydrofuran / 0.25 h / 0 °C 13: 75percent aq. CH3COOH / tetrahydrofuran / 0 - 5 °C 14: 68 percent / diethyl cyanophosphonate, Et3N / dimethylformamide / 0.5 h / 0 °C 15: 86 percent / (COCl)2, (CH3)2SO / CH2Cl2 / 0.33 h / -78 °C 16: 69 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 2.5 h / 0 °C 17: 100 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), H2O / CH2Cl2 / 0.5 h / Ambient temperature 18: 64 percent / CF3COOH / 2.5 h / Ambient temperature View Scheme

1: 1.) KH, 2.) tetrabutylammonium chloride, 18-crown-6 / 1.) THF, 15 min, 2.) THF, RT, 20 min 2: 86 percent / sodium naphthalenide / 1,2-dimethoxy-ethane / 0.67 h / -78 °C 3: 99 percent / K2CO3 / tetrahydrofuran; toluene 4: 85 percent / MeI, H2O / acetonitrile / Ambient temperature 5: 1.) t-BuLi, 2.) dineopentylzinc 6: (CH3)2SO, pyridine, CF3COOH, dicyclohexylcarbodiimide (DCC) / benzene / 0.5 h / Ambient temperature 7: benzene; diethyl ether / 0.33 h 8: n-Bu4NF / tetrahydrofuran / 0.25 h / 0 °C 9: 75percent aq. CH3COOH / tetrahydrofuran / 0 - 5 °C 10: 68 percent / diethyl cyanophosphonate, Et3N / dimethylformamide / 0.5 h / 0 °C 11: 86 percent / (COCl)2, (CH3)2SO / CH2Cl2 / 0.33 h / -78 °C 12: 69 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / 2.5 h / 0 °C 13: 100 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), H2O / CH2Cl2 / 0.5 h / Ambient temperature 14: 64 percent / CF3COOH / 2.5 h / Ambient temperature View Scheme

6: 1.) <O> 7: 1.) n-Bu4NF, 2.) aq.AcOH / 1.) THF, 0 deg C 8: 68 percent / diethyl cyanophosphate / dimethylformamide / 0 °C 9: 86 percent / <O> 10: 69 percent / lithium hexamethyldisilazide / tetrahydrofuran / -78 - 0 °C 11: 1.) DDQ, 2.) aq.HCl / 1.) CH2Cl2, H2O 12: 64 percent / trifluoroacetic acid / 2.5 h / Ambient temperature View Scheme

5: 1.) <O> 6: 1.) n-Bu4NF, 2.) aq.AcOH / 1.) THF, 0 deg C 7: 68 percent / diethyl cyanophosphate / dimethylformamide / 0 °C 8: 86 percent / <O> 9: 69 percent / lithium hexamethyldisilazide / tetrahydrofuran / -78 - 0 °C 10: 1.) DDQ, 2.) aq.HCl / 1.) CH2Cl2, H2O 11: 64 percent / trifluoroacetic acid / 2.5 h / Ambient temperature View Scheme