1: 97 percent / PCC, NaOAc 2: 71 percent / tetrahydrofuran 3: 90 percent / PCC / CH2Cl2 4: 80 percent / NaH / tetrahydrofuran / 25 °C 5: 76 percent / HOAc, H2O / 25 °C 6: 75 percent / KOH, NaHCO3 / tetrahydrofuran; ethanol / 25 °C View Scheme

Multi-step reaction with 10 steps 1: 94 percent / cupric sulfate, p-toluenesulfonic acid / 24 h / Ambient temperature2: 74 percent / diisobutylaluminium hydride / diethyl ether; hexane / 0.5 h / -90 °C3: 1.) Mg, 2.) zinc bromide / 1.) THF, RT, 1.5 h, 2.) CH2Cl2, -100 deg C, 1 h4: 81 percent / dicyclohexylcarbodiimide (DCC), (dimethylamino)pyridine (DMAP) / CH2Cl2 / Ambient temperature5: lithium diisopropylamide (LDA), trimethylsilyl chloride (TMSCl), pyridine / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C6: diethyl ether / 0 °C7: 77 percent / diisobutylaluminium hydride / CH2Cl2; hexane / 0.5 h / -20 °C8: 60 percent / triphenylphosphine, imidazole, diisopropylamine, iodine / diethyl ether; acetonitrile / 3 h / Ambient temperature9: 70 percent / azoisobutyronitrile, tributyltin hydride / aq. ethanol / 12 h / Ambient temperature10: 70 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 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 17 steps 1: 43 percent / ethylaluminium dichloride / CH2Cl2; hexane / 12 h / Ambient temperature2: 72 percent / iodine / tetrahydrofuran; H2O / 4 h / 0 - 20 °C3: 82 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / Ambient temperature4: 91 percent / lithium aluminium hydride / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C5: pyridine / 2 h / 0 - 20 °C6: 100 percent / xylene / 12 h / Heating7: 90 percent / N-methylmorpholine N-oxide, OsO4 / acetone; H2O / 24 h / Ambient temperature8: 94 percent / cupric sulfate, p-toluenesulfonic acid / 24 h / Ambient temperature9: 74 percent / diisobutylaluminium hydride / diethyl ether; hexane / 0.5 h / -90 °C10: 1.) Mg, 2.) zinc bromide / 1.) THF, RT, 1.5 h, 2.) CH2Cl2, -100 deg C, 1 h11: 81 percent / dicyclohexylcarbodiimide (DCC), (dimethylamino)pyridine (DMAP) / CH2Cl2 / Ambient temperature12: lithium diisopropylamide (LDA), trimethylsilyl chloride (TMSCl), pyridine / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C13: diethyl ether / 0 °C14: 77 percent / diisobutylaluminium hydride / CH2Cl2; hexane / 0.5 h / -20 °C15: 60 percent / triphenylphosphine, imidazole, diisopropylamine, iodine / diethyl ether; acetonitrile / 3 h / Ambient temperature16: 70 percent / azoisobutyronitrile, tributyltin hydride / aq. ethanol / 12 h / Ambient temperature17: 70 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature  

Multi-step reaction with 11 steps 1: 90 percent / N-methylmorpholine N-oxide, OsO4 / acetone; H2O / 24 h / Ambient temperature2: 94 percent / cupric sulfate, p-toluenesulfonic acid / 24 h / Ambient temperature3: 74 percent / diisobutylaluminium hydride / diethyl ether; hexane / 0.5 h / -90 °C4: 1.) Mg, 2.) zinc bromide / 1.) THF, RT, 1.5 h, 2.) CH2Cl2, -100 deg C, 1 h5: 81 percent / dicyclohexylcarbodiimide (DCC), (dimethylamino)pyridine (DMAP) / CH2Cl2 / Ambient temperature6: lithium diisopropylamide (LDA), trimethylsilyl chloride (TMSCl), pyridine / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C7: diethyl ether / 0 °C8: 77 percent / diisobutylaluminium hydride / CH2Cl2; hexane / 0.5 h / -20 °C9: 60 percent / triphenylphosphine, imidazole, diisopropylamine, iodine / diethyl ether; acetonitrile / 3 h / Ambient temperature10: 70 percent / azoisobutyronitrile, tributyltin hydride / aq. ethanol / 12 h / Ambient temperature11: 70 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature  

With  Celite; sodium acetate; pyridinium chlorochromate in  dichloromethane 1.5 h;  Ambient temperature;   

Multi-step reaction with 2 steps 1: 97 percent / PCC, NaOAc2: 71 percent / tetrahydrofuran