1: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C 3: tetrahydrofuran; hexane 4: 97 percent / CF3COOH / CH2Cl2 / 1 h / Ambient temperature 5: PDC, 4 Angstroem molecular sieves / dimethylformamide / 20 h / Ambient temperature 7: 3 N LiOH / methanol / 1 h / Heating 8: Li, liq. NH3 / tetrahydrofuran / 0.5 h / -78 °C View Scheme

1: tetrahydrofuran; hexane 2: 97 percent / CF3COOH / CH2Cl2 / 1 h / Ambient temperature 3: PDC, 4 Angstroem molecular sieves / dimethylformamide / 20 h / Ambient temperature 5: 3 N LiOH / methanol / 1 h / Heating 6: Li, liq. NH3 / tetrahydrofuran / 0.5 h / -78 °C View Scheme

1: 95 percent / Fe(O), Et3N, HMPA / diethyl ether; tetrahydrofuran / 1.) r.t., 10 min, 2.) r.t., 2 h 2: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C 4: tetrahydrofuran; hexane 5: 97 percent / CF3COOH / CH2Cl2 / 1 h / Ambient temperature 6: PDC, 4 Angstroem molecular sieves / dimethylformamide / 20 h / Ambient temperature 8: 3 N LiOH / methanol / 1 h / Heating 9: Li, liq. NH3 / tetrahydrofuran / 0.5 h / -78 °C View Scheme

1.1: 2,6-dimethylpyridine / dichloromethane / 12.25 h / 0 - 20 °C / Inert atmosphere 2.1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere 3.1: tert.-butyl lithium; copper (I) cyanide; lithium bromide; zinc dibromide / tetrahydrofuran; pentane / -78 °C / Inert atmosphere 3.2: 0.5 h / -78 °C / Inert atmosphere 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 4.2: 0.5 h / -78 °C / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere 5.2: 3 h / 0 - 20 °C / Inert atmosphere 6.1: water; acetic acid / 5 h / 45 °C / Inert atmosphere 7.1: toluene / 5 h / 20 °C / Inert atmosphere; Sealed reactor 8.1: toluene / 204 h / 135 °C / 1368.09 Torr / Inert atmosphere; Molecular sieve; Sealed reactor 9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 20 °C / Inert atmosphere 10.1: potassium carbonate / toluene / 17 h / 120 °C / Inert atmosphere; Sealed tube 11.1: hydrogenchloride; water / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere 12.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / dichloromethane / 83 h / -20 °C / Inert atmosphere 12.2: 0.5 h / -20 °C / Inert atmosphere 13.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 2.5 h / 20 °C / Inert atmosphere 14.1: methanol; diethyl ether; benzene / 0.5 h / 20 °C / Inert atmosphere 15.1: ammonium cerium (IV) nitrate; water / acetonitrile / 1.5 h / 20 °C / Inert atmosphere 16.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1 h / 0 °C / Inert atmosphere 17.1: water; potassium hydroxide / tert-butyl alcohol / 6.5 h / 120 °C / Inert atmosphere 17.2: 20 °C / Inert atmosphere View Scheme

1.1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere 2.1: tert.-butyl lithium; copper (I) cyanide; lithium bromide; zinc dibromide / tetrahydrofuran; pentane / -78 °C / Inert atmosphere 2.2: 0.5 h / -78 °C / Inert atmosphere 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 3.2: 0.5 h / -78 °C / Inert atmosphere 4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere 4.2: 3 h / 0 - 20 °C / Inert atmosphere 5.1: water; acetic acid / 5 h / 45 °C / Inert atmosphere 6.1: toluene / 5 h / 20 °C / Inert atmosphere; Sealed reactor 7.1: toluene / 204 h / 135 °C / 1368.09 Torr / Inert atmosphere; Molecular sieve; Sealed reactor 8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 20 °C / Inert atmosphere 9.1: potassium carbonate / toluene / 17 h / 120 °C / Inert atmosphere; Sealed tube 10.1: hydrogenchloride; water / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere 11.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / dichloromethane / 83 h / -20 °C / Inert atmosphere 11.2: 0.5 h / -20 °C / Inert atmosphere 12.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 2.5 h / 20 °C / Inert atmosphere 13.1: methanol; diethyl ether; benzene / 0.5 h / 20 °C / Inert atmosphere 14.1: ammonium cerium (IV) nitrate; water / acetonitrile / 1.5 h / 20 °C / Inert atmosphere 15.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1 h / 0 °C / Inert atmosphere 16.1: water; potassium hydroxide / tert-butyl alcohol / 6.5 h / 120 °C / Inert atmosphere 16.2: 20 °C / Inert atmosphere View Scheme

1.1: tert.-butyl lithium; copper (I) cyanide; lithium bromide; zinc dibromide / tetrahydrofuran; pentane / -78 °C / Inert atmosphere 1.2: 0.5 h / -78 °C / Inert atmosphere 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 2.2: 0.5 h / -78 °C / Inert atmosphere 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere 3.2: 3 h / 0 - 20 °C / Inert atmosphere 4.1: water; acetic acid / 5 h / 45 °C / Inert atmosphere 5.1: toluene / 5 h / 20 °C / Inert atmosphere; Sealed reactor 6.1: toluene / 204 h / 135 °C / 1368.09 Torr / Inert atmosphere; Molecular sieve; Sealed reactor 7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 20 °C / Inert atmosphere 8.1: potassium carbonate / toluene / 17 h / 120 °C / Inert atmosphere; Sealed tube 9.1: hydrogenchloride; water / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere 10.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / dichloromethane / 83 h / -20 °C / Inert atmosphere 10.2: 0.5 h / -20 °C / Inert atmosphere 11.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 2.5 h / 20 °C / Inert atmosphere 12.1: methanol; diethyl ether; benzene / 0.5 h / 20 °C / Inert atmosphere 13.1: ammonium cerium (IV) nitrate; water / acetonitrile / 1.5 h / 20 °C / Inert atmosphere 14.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1 h / 0 °C / Inert atmosphere 15.1: water; potassium hydroxide / tert-butyl alcohol / 6.5 h / 120 °C / Inert atmosphere 15.2: 20 °C / Inert atmosphere View Scheme

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere 1.2: 0.5 h / -78 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere 2.2: 3 h / 0 - 20 °C / Inert atmosphere 3.1: water; acetic acid / 5 h / 45 °C / Inert atmosphere 4.1: toluene / 5 h / 20 °C / Inert atmosphere; Sealed reactor 5.1: toluene / 204 h / 135 °C / 1368.09 Torr / Inert atmosphere; Molecular sieve; Sealed reactor 6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 20 °C / Inert atmosphere 7.1: potassium carbonate / toluene / 17 h / 120 °C / Inert atmosphere; Sealed tube 8.1: hydrogenchloride; water / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere 9.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / dichloromethane / 83 h / -20 °C / Inert atmosphere 9.2: 0.5 h / -20 °C / Inert atmosphere 10.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 2.5 h / 20 °C / Inert atmosphere 11.1: methanol; diethyl ether; benzene / 0.5 h / 20 °C / Inert atmosphere 12.1: ammonium cerium (IV) nitrate; water / acetonitrile / 1.5 h / 20 °C / Inert atmosphere 13.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1 h / 0 °C / Inert atmosphere 14.1: water; potassium hydroxide / tert-butyl alcohol / 6.5 h / 120 °C / Inert atmosphere 14.2: 20 °C / Inert atmosphere View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere 1.2: 3 h / 0 - 20 °C / Inert atmosphere 2.1: water; acetic acid / 5 h / 45 °C / Inert atmosphere 3.1: toluene / 5 h / 20 °C / Inert atmosphere; Sealed reactor 4.1: toluene / 204 h / 135 °C / 1368.09 Torr / Inert atmosphere; Molecular sieve; Sealed reactor 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 20 °C / Inert atmosphere 6.1: potassium carbonate / toluene / 17 h / 120 °C / Inert atmosphere; Sealed tube 7.1: hydrogenchloride; water / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere 8.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / dichloromethane / 83 h / -20 °C / Inert atmosphere 8.2: 0.5 h / -20 °C / Inert atmosphere 9.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 2.5 h / 20 °C / Inert atmosphere 10.1: methanol; diethyl ether; benzene / 0.5 h / 20 °C / Inert atmosphere 11.1: ammonium cerium (IV) nitrate; water / acetonitrile / 1.5 h / 20 °C / Inert atmosphere 12.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1 h / 0 °C / Inert atmosphere 13.1: water; potassium hydroxide / tert-butyl alcohol / 6.5 h / 120 °C / Inert atmosphere 13.2: 20 °C / Inert atmosphere View Scheme

1.1: water; acetic acid / 5 h / 45 °C / Inert atmosphere 2.1: toluene / 5 h / 20 °C / Inert atmosphere; Sealed reactor 3.1: toluene / 204 h / 135 °C / 1368.09 Torr / Inert atmosphere; Molecular sieve; Sealed reactor 4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 20 °C / Inert atmosphere 5.1: potassium carbonate / toluene / 17 h / 120 °C / Inert atmosphere; Sealed tube 6.1: hydrogenchloride; water / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere 7.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / dichloromethane / 83 h / -20 °C / Inert atmosphere 7.2: 0.5 h / -20 °C / Inert atmosphere 8.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 2.5 h / 20 °C / Inert atmosphere 9.1: methanol; diethyl ether; benzene / 0.5 h / 20 °C / Inert atmosphere 10.1: ammonium cerium (IV) nitrate; water / acetonitrile / 1.5 h / 20 °C / Inert atmosphere 11.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1 h / 0 °C / Inert atmosphere 12.1: water; potassium hydroxide / tert-butyl alcohol / 6.5 h / 120 °C / Inert atmosphere 12.2: 20 °C / Inert atmosphere View Scheme

1.1: toluene / 5 h / 20 °C / Inert atmosphere; Sealed reactor 2.1: toluene / 204 h / 135 °C / 1368.09 Torr / Inert atmosphere; Molecular sieve; Sealed reactor 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / 20 °C / Inert atmosphere 4.1: potassium carbonate / toluene / 17 h / 120 °C / Inert atmosphere; Sealed tube 5.1: hydrogenchloride; water / tetrahydrofuran / 8 h / 20 °C / Inert atmosphere 6.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / dichloromethane / 83 h / -20 °C / Inert atmosphere 6.2: 0.5 h / -20 °C / Inert atmosphere 7.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 2.5 h / 20 °C / Inert atmosphere 8.1: methanol; diethyl ether; benzene / 0.5 h / 20 °C / Inert atmosphere 9.1: ammonium cerium (IV) nitrate; water / acetonitrile / 1.5 h / 20 °C / Inert atmosphere 10.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1 h / 0 °C / Inert atmosphere 11.1: water; potassium hydroxide / tert-butyl alcohol / 6.5 h / 120 °C / Inert atmosphere 11.2: 20 °C / Inert atmosphere View Scheme