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

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

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

1: lithium diisopropylamide (LDA), trimethylsilyl chloride (TMSCl), pyridine / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C 2: diethyl ether / 0 °C 3: 77 percent / diisobutylaluminium hydride / CH2Cl2; hexane / 0.5 h / -20 °C 4: 60 percent / triphenylphosphine, imidazole, diisopropylamine, iodine / diethyl ether; acetonitrile / 3 h / Ambient temperature 5: 70 percent / azoisobutyronitrile, tributyltin hydride / aq. ethanol / 12 h / Ambient temperature 6: 70 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature 7: 97 percent / pyridinium chlorochromate, sodium acetate, Celite / CH2Cl2 / 1.5 h / Ambient temperature 8: 71 percent / tetrahydrofuran; diethyl ether / 1.8 h / -78 - 0 °C 9: 95 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 10: 1.) sodium hydride / 1.) THF, RT, 1 h 2.) RT, overnight 11: 80 percent / 80percent aq CH3COOH / Ambient temperature 12: 77 percent / 1N aq NaHCO3, 1N aq KOH / ethanol; tetrahydrofuran / 4.5 h / 0 °C View Scheme

1: p-toluenesulfonic acid 2: p-toluenesulfonic acid / acetone / 23 °C 3: 1.) MeLi / 1.) THF, -78 deg C 4: toluene / Irradiation 5: 1.) OsO4, NaIO4, 2.) NaBH4 / 1.) THF,H2O, 2.) ethanol 6: pyridine 7: dimethylformamide 8: CH3CO3H, NaHCO3 / CH2Cl2 9: 1.) LDA / 1.) THF, 0 deg C, 15 min 10: pyridine / 23 °C 11: Li, NH3 / tetrahydrofuran / -78 °C 12: 2.) K2CO3 / 1.) 1,2-dichloroethane, 70 deg C, 24 h, 2.) MeOH, 0 deg C 13: 1.) LiN(SiMe3)2 / 1.) dioxane 14: 80percent HOAc 15: Na2CO3, KOH / ethanol; tetrahydrofuran View Scheme

1: 1.) OsO4, NaIO4, 2.) NaBH4 / 1.) THF,H2O, 2.) ethanol 2: pyridine 3: dimethylformamide 4: CH3CO3H, NaHCO3 / CH2Cl2 5: 1.) LDA / 1.) THF, 0 deg C, 15 min 6: pyridine / 23 °C 7: Li, NH3 / tetrahydrofuran / -78 °C 8: 2.) K2CO3 / 1.) 1,2-dichloroethane, 70 deg C, 24 h, 2.) MeOH, 0 deg C 9: 1.) LiN(SiMe3)2 / 1.) dioxane 10: 80percent HOAc 11: Na2CO3, KOH / ethanol; tetrahydrofuran View Scheme

1: pyridine 2: dimethylformamide 3: CH3CO3H, NaHCO3 / CH2Cl2 4: 1.) LDA / 1.) THF, 0 deg C, 15 min 5: pyridine / 23 °C 6: Li, NH3 / tetrahydrofuran / -78 °C 7: 2.) K2CO3 / 1.) 1,2-dichloroethane, 70 deg C, 24 h, 2.) MeOH, 0 deg C 8: 1.) LiN(SiMe3)2 / 1.) dioxane 9: 80percent HOAc 10: Na2CO3, KOH / ethanol; tetrahydrofuran View Scheme

1: 1.) LiN(SiMe3)2 / 1.) dioxane 2: 80percent HOAc 3: Na2CO3, KOH / ethanol; tetrahydrofuran View Scheme

1: dimethylformamide 2: CH3CO3H, NaHCO3 / CH2Cl2 3: 1.) LDA / 1.) THF, 0 deg C, 15 min 4: pyridine / 23 °C 5: Li, NH3 / tetrahydrofuran / -78 °C 6: 2.) K2CO3 / 1.) 1,2-dichloroethane, 70 deg C, 24 h, 2.) MeOH, 0 deg C 7: 1.) LiN(SiMe3)2 / 1.) dioxane 8: 80percent HOAc 9: Na2CO3, KOH / ethanol; tetrahydrofuran View Scheme

1: toluene / Irradiation 2: 1.) OsO4, NaIO4, 2.) NaBH4 / 1.) THF,H2O, 2.) ethanol 3: pyridine 4: dimethylformamide 5: CH3CO3H, NaHCO3 / CH2Cl2 6: 1.) LDA / 1.) THF, 0 deg C, 15 min 7: pyridine / 23 °C 8: Li, NH3 / tetrahydrofuran / -78 °C 9: 2.) K2CO3 / 1.) 1,2-dichloroethane, 70 deg C, 24 h, 2.) MeOH, 0 deg C 10: 1.) LiN(SiMe3)2 / 1.) dioxane 11: 80percent HOAc 12: Na2CO3, KOH / ethanol; tetrahydrofuran View Scheme