1: 82 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / Ambient temperature 2: 91 percent / lithium aluminium hydride / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C 3: pyridine / 2 h / 0 - 20 °C 4: 100 percent / xylene / 12 h / Heating 5: 90 percent / N-methylmorpholine N-oxide, OsO4 / acetone; H2O / 24 h / Ambient temperature 6: 94 percent / cupric sulfate, p-toluenesulfonic acid / 24 h / Ambient temperature 7: 74 percent / diisobutylaluminium hydride / diethyl ether; hexane / 0.5 h / -90 °C 8: 1.) Mg, 2.) zinc bromide / 1.) THF, RT, 1.5 h, 2.) CH2Cl2, -100 deg C, 1 h 9: 81 percent / dicyclohexylcarbodiimide (DCC), (dimethylamino)pyridine (DMAP) / CH2Cl2 / Ambient temperature 10: lithium diisopropylamide (LDA), trimethylsilyl chloride (TMSCl), pyridine / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C 11: diethyl ether / 0 °C 12: 77 percent / diisobutylaluminium hydride / CH2Cl2; hexane / 0.5 h / -20 °C 13: 60 percent / triphenylphosphine, imidazole, diisopropylamine, iodine / diethyl ether; acetonitrile / 3 h / Ambient temperature 14: 70 percent / azoisobutyronitrile, tributyltin hydride / aq. ethanol / 12 h / Ambient temperature 15: 70 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature 16: 97 percent / pyridinium chlorochromate, sodium acetate, Celite / CH2Cl2 / 1.5 h / Ambient temperature 17: 71 percent / tetrahydrofuran; diethyl ether / 1.8 h / -78 - 0 °C 18: 95 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 19: 1.) sodium hydride / 1.) THF, RT, 1 h 2.) RT, overnight 20: 80 percent / 80percent aq CH3COOH / Ambient temperature 21: 77 percent / 1N aq NaHCO3, 1N aq KOH / ethanol; tetrahydrofuran / 4.5 h / 0 °C View Scheme

Multi-step reaction with 5 steps 1: 82 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / Ambient temperature2: 91 percent / lithium aluminium hydride / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C3: pyridine / 2 h / 0 - 20 °C4: 100 percent / xylene / 12 h / Heating5: 90 percent / N-methylmorpholine N-oxide, OsO4 / acetone; H2O / 24 h / Ambient temperature  

Multi-step reaction with 12 steps 1: 82 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / Ambient temperature2: 91 percent / lithium aluminium hydride / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C3: pyridine / 2 h / 0 - 20 °C4: 100 percent / xylene / 12 h / Heating5: 90 percent / N-methylmorpholine N-oxide, OsO4 / acetone; H2O / 24 h / Ambient temperature6: 94 percent / cupric sulfate, p-toluenesulfonic acid / 24 h / Ambient temperature7: 74 percent / diisobutylaluminium hydride / diethyl ether; hexane / 0.5 h / -90 °C8: 1.) Mg, 2.) zinc bromide / 1.) THF, RT, 1.5 h, 2.) CH2Cl2, -100 deg C, 1 h9: 81 percent / dicyclohexylcarbodiimide (DCC), (dimethylamino)pyridine (DMAP) / CH2Cl2 / Ambient temperature10: lithium diisopropylamide (LDA), trimethylsilyl chloride (TMSCl), pyridine / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C11: diethyl ether / 0 °C12: 77 percent / diisobutylaluminium hydride / CH2Cl2; hexane / 0.5 h / -20 °C  

Multi-step reaction with 13 steps 1: 82 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / Ambient temperature2: 91 percent / lithium aluminium hydride / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C3: pyridine / 2 h / 0 - 20 °C4: 100 percent / xylene / 12 h / Heating5: 90 percent / N-methylmorpholine N-oxide, OsO4 / acetone; H2O / 24 h / Ambient temperature6: 94 percent / cupric sulfate, p-toluenesulfonic acid / 24 h / Ambient temperature7: 74 percent / diisobutylaluminium hydride / diethyl ether; hexane / 0.5 h / -90 °C8: 1.) Mg, 2.) zinc bromide / 1.) THF, RT, 1.5 h, 2.) CH2Cl2, -100 deg C, 1 h9: 81 percent / dicyclohexylcarbodiimide (DCC), (dimethylamino)pyridine (DMAP) / CH2Cl2 / Ambient temperature10: lithium diisopropylamide (LDA), trimethylsilyl chloride (TMSCl), pyridine / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C11: diethyl ether / 0 °C12: 77 percent / diisobutylaluminium hydride / CH2Cl2; hexane / 0.5 h / -20 °C13: 60 percent / triphenylphosphine, imidazole, diisopropylamine, iodine / diethyl ether; acetonitrile / 3 h / Ambient temperature  

Multi-step reaction with 15 steps 1: 82 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / Ambient temperature2: 91 percent / lithium aluminium hydride / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C3: pyridine / 2 h / 0 - 20 °C4: 100 percent / xylene / 12 h / Heating5: 90 percent / N-methylmorpholine N-oxide, OsO4 / acetone; H2O / 24 h / Ambient temperature6: 94 percent / cupric sulfate, p-toluenesulfonic acid / 24 h / Ambient temperature7: 74 percent / diisobutylaluminium hydride / diethyl ether; hexane / 0.5 h / -90 °C8: 1.) Mg, 2.) zinc bromide / 1.) THF, RT, 1.5 h, 2.) CH2Cl2, -100 deg C, 1 h9: 81 percent / dicyclohexylcarbodiimide (DCC), (dimethylamino)pyridine (DMAP) / CH2Cl2 / Ambient temperature10: lithium diisopropylamide (LDA), trimethylsilyl chloride (TMSCl), pyridine / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C11: diethyl ether / 0 °C12: 77 percent / diisobutylaluminium hydride / CH2Cl2; hexane / 0.5 h / -20 °C13: 60 percent / triphenylphosphine, imidazole, diisopropylamine, iodine / diethyl ether; acetonitrile / 3 h / Ambient temperature14: 70 percent / azoisobutyronitrile, tributyltin hydride / aq. ethanol / 12 h / Ambient temperature15: 70 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature  

Multi-step reaction with 16 steps 1: 82 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / Ambient temperature2: 91 percent / lithium aluminium hydride / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C3: pyridine / 2 h / 0 - 20 °C4: 100 percent / xylene / 12 h / Heating5: 90 percent / N-methylmorpholine N-oxide, OsO4 / acetone; H2O / 24 h / Ambient temperature6: 94 percent / cupric sulfate, p-toluenesulfonic acid / 24 h / Ambient temperature7: 74 percent / diisobutylaluminium hydride / diethyl ether; hexane / 0.5 h / -90 °C8: 1.) Mg, 2.) zinc bromide / 1.) THF, RT, 1.5 h, 2.) CH2Cl2, -100 deg C, 1 h9: 81 percent / dicyclohexylcarbodiimide (DCC), (dimethylamino)pyridine (DMAP) / CH2Cl2 / Ambient temperature10: lithium diisopropylamide (LDA), trimethylsilyl chloride (TMSCl), pyridine / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C11: diethyl ether / 0 °C12: 77 percent / diisobutylaluminium hydride / CH2Cl2; hexane / 0.5 h / -20 °C13: 60 percent / triphenylphosphine, imidazole, diisopropylamine, iodine / diethyl ether; acetonitrile / 3 h / Ambient temperature14: 70 percent / azoisobutyronitrile, tributyltin hydride / aq. ethanol / 12 h / Ambient temperature15: 70 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature16: 97 percent / pyridinium chlorochromate, sodium acetate, Celite / CH2Cl2 / 1.5 h / Ambient temperature  

Multi-step reaction with 17 steps 1: 82 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / Ambient temperature2: 91 percent / lithium aluminium hydride / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C3: pyridine / 2 h / 0 - 20 °C4: 100 percent / xylene / 12 h / Heating5: 90 percent / N-methylmorpholine N-oxide, OsO4 / acetone; H2O / 24 h / Ambient temperature6: 94 percent / cupric sulfate, p-toluenesulfonic acid / 24 h / Ambient temperature7: 74 percent / diisobutylaluminium hydride / diethyl ether; hexane / 0.5 h / -90 °C8: 1.) Mg, 2.) zinc bromide / 1.) THF, RT, 1.5 h, 2.) CH2Cl2, -100 deg C, 1 h9: 81 percent / dicyclohexylcarbodiimide (DCC), (dimethylamino)pyridine (DMAP) / CH2Cl2 / Ambient temperature10: lithium diisopropylamide (LDA), trimethylsilyl chloride (TMSCl), pyridine / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C11: diethyl ether / 0 °C12: 77 percent / diisobutylaluminium hydride / CH2Cl2; hexane / 0.5 h / -20 °C13: 60 percent / triphenylphosphine, imidazole, diisopropylamine, iodine / diethyl ether; acetonitrile / 3 h / Ambient temperature14: 70 percent / azoisobutyronitrile, tributyltin hydride / aq. ethanol / 12 h / Ambient temperature15: 70 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature16: 97 percent / pyridinium chlorochromate, sodium acetate, Celite / CH2Cl2 / 1.5 h / Ambient temperature17: 71 percent / tetrahydrofuran; diethyl ether / 1.8 h / -78 - 0 °C  

Multi-step reaction with 4 steps 1: 82 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / Ambient temperature2: 91 percent / lithium aluminium hydride / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C3: pyridine / 2 h / 0 - 20 °C4: 100 percent / xylene / 12 h / Heating  

With  iodine in  tetrahydrofuran; water T=0 - 20°C; 4 h;   

Multi-step reaction with 2 steps 1: 43 percent / ethylaluminium dichloride / CH2Cl2; hexane / 12 h / Ambient temperature2: 72 percent / iodine / tetrahydrofuran; H2O / 4 h / 0 - 20 °C