potassium hydroxide; sodium hydrogencarbonate in tetrahydrofuran; ethanol T=0°C; 4.5 h;

1: 80 percent / NaH / tetrahydrofuran / 25 °C 2: 76 percent / HOAc, H2O / 25 °C 3: 75 percent / KOH, NaHCO3 / tetrahydrofuran; ethanol / 25 °C View Scheme

1: HBr, Ac2O 2: 1.) Hydrogen, Et3N 2.) MeONa / 2.) MeOH 3: 1.) HC(OEt)3 / 1.) AcOH / 1.) EtOAc 2.) 250 deg C 4: 82 percent / xylene / 18 h / Heating 5: 81 percent / I2 / tetrahydrofuran; H2O / 0 °C 6: 86 percent / NaBH4 / ethanol 7: 93 percent / imidazole / dimethylformamide 8: 94 percent / xylene / 7 h / Heating 9: 81 percent / tetrahydrofuran / -78 °C 10: 85 percent / N-Methylmorpholine-N-oxide, OsO4 11: 93 percent / anhydr. CuSO4, TsOH 12: 75 percent / tetrahydrofuran / 24 h / Ambient temperature 13: 87 percent / Bu4NF / tetrahydrofuran / 4 h / Ambient temperature 14: 80 percent / PCC,molecular sieve / CH2Cl2 / 1 h / Ambient temperature 15: 1.) n-BuLi / 2.) THF, -40 to -30 deg C, 2 h and 0 deg C, 30 min. 16: 50percent aq. AcOH / 72 h / Ambient temperature View Scheme

1: 1.) HC(OEt)3 / 1.) AcOH / 1.) EtOAc 2.) 250 deg C 2: 82 percent / xylene / 18 h / Heating 3: 81 percent / I2 / tetrahydrofuran; H2O / 0 °C 4: 86 percent / NaBH4 / ethanol 5: 93 percent / imidazole / dimethylformamide 6: 94 percent / xylene / 7 h / Heating 7: 81 percent / tetrahydrofuran / -78 °C 8: 85 percent / N-Methylmorpholine-N-oxide, OsO4 9: 93 percent / anhydr. CuSO4, TsOH 10: 75 percent / tetrahydrofuran / 24 h / Ambient temperature 11: 87 percent / Bu4NF / tetrahydrofuran / 4 h / Ambient temperature 12: 80 percent / PCC,molecular sieve / CH2Cl2 / 1 h / Ambient temperature 13: 1.) n-BuLi / 2.) THF, -40 to -30 deg C, 2 h and 0 deg C, 30 min. 14: 50percent aq. AcOH / 72 h / Ambient temperature View Scheme

1: NaCN / acetic acid / 16 h View Scheme

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

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

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

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

1: 1.) n-BuLi, BF3 / 1.) THF, hexane, ether, -78 deg C, 20 min, 2.) 30 min 2: 85 percent / (-)-alpine borane / tetrahydrofuran / 24 h / Ambient temperature 3: 92 percent / LiAlH4, sodium methoxide / tetrahydrofuran / 4.5 h / Heating 4: 81 percent / dicyclohexylcarbodiimide (DCC), (dimethylamino)pyridine (DMAP) / CH2Cl2 / Ambient temperature 5: lithium diisopropylamide (LDA), trimethylsilyl chloride (TMSCl), pyridine / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C 6: diethyl ether / 0 °C 7: 77 percent / diisobutylaluminium hydride / CH2Cl2; hexane / 0.5 h / -20 °C 8: 60 percent / triphenylphosphine, imidazole, diisopropylamine, iodine / diethyl ether; acetonitrile / 3 h / Ambient temperature 9: 70 percent / azoisobutyronitrile, tributyltin hydride / aq. ethanol / 12 h / Ambient temperature 10: 70 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature 11: 97 percent / pyridinium chlorochromate, sodium acetate, Celite / CH2Cl2 / 1.5 h / Ambient temperature 12: 71 percent / tetrahydrofuran; diethyl ether / 1.8 h / -78 - 0 °C 13: 95 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 14: 1.) sodium hydride / 1.) THF, RT, 1 h 2.) RT, overnight 15: 80 percent / 80percent aq CH3COOH / Ambient temperature 16: 77 percent / 1N aq NaHCO3, 1N aq KOH / ethanol; tetrahydrofuran / 4.5 h / 0 °C View Scheme