1: 75 percent / n-Bu4NF / tetrahydrofuran 2: 97 percent / PCC, NaOAc 3: 71 percent / tetrahydrofuran 4: 90 percent / PCC / CH2Cl2 5: 80 percent / NaH / tetrahydrofuran / 25 °C 6: 76 percent / HOAc, H2O / 25 °C 7: 75 percent / KOH, NaHCO3 / tetrahydrofuran; ethanol / 25 °C View Scheme

1: 86 percent / imidazole / dimethylformamide / Ambient temperature 2: 84 percent / diisobutylaluminium hydride / CH2Cl2; hexane / 1.) -78 deg C, 3 h 2.) -20 deg C, 2 h 3: 97 percent / pyridine / Ambient temperature 4: 90 percent / NaI / butan-2-one / 1.5 h / Heating 5: 81 percent / hexamethylphosphoric acid triamide / 0.5 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: 80 percent / 80percent aq CH3COOH / Ambient temperature 2: 77 percent / 1N aq NaHCO3, 1N aq KOH / ethanol; tetrahydrofuran / 4.5 h / 0 °C View Scheme

1: 84 percent / diisobutylaluminium hydride / CH2Cl2; hexane / 1.) -78 deg C, 3 h 2.) -20 deg C, 2 h 2: 97 percent / pyridine / Ambient temperature 3: 90 percent / NaI / butan-2-one / 1.5 h / Heating 4: 81 percent / hexamethylphosphoric acid triamide / 0.5 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: 66 percent / diethyl ether / 2 h / Ambient temperature 2: 43 percent / ethylaluminium dichloride / CH2Cl2; hexane / 12 h / Ambient temperature 3: 72 percent / iodine / tetrahydrofuran; H2O / 4 h / 0 - 20 °C 4: 82 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / Ambient temperature 5: 91 percent / lithium aluminium hydride / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C 6: pyridine / 2 h / 0 - 20 °C 7: 100 percent / xylene / 12 h / Heating 8: 90 percent / N-methylmorpholine N-oxide, OsO4 / acetone; H2O / 24 h / Ambient temperature 9: 94 percent / cupric sulfate, p-toluenesulfonic acid / 24 h / Ambient temperature 10: 74 percent / diisobutylaluminium hydride / diethyl ether; hexane / 0.5 h / -90 °C 11: 1.) Mg, 2.) zinc bromide / 1.) THF, RT, 1.5 h, 2.) CH2Cl2, -100 deg C, 1 h 12: 81 percent / dicyclohexylcarbodiimide (DCC), (dimethylamino)pyridine (DMAP) / CH2Cl2 / Ambient temperature 13: lithium diisopropylamide (LDA), trimethylsilyl chloride (TMSCl), pyridine / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C 14: diethyl ether / 0 °C 15: 77 percent / diisobutylaluminium hydride / CH2Cl2; hexane / 0.5 h / -20 °C 16: 60 percent / triphenylphosphine, imidazole, diisopropylamine, iodine / diethyl ether; acetonitrile / 3 h / Ambient temperature 17: 70 percent / azoisobutyronitrile, tributyltin hydride / aq. ethanol / 12 h / Ambient temperature 18: 70 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature 19: 97 percent / pyridinium chlorochromate, sodium acetate, Celite / CH2Cl2 / 1.5 h / Ambient temperature 20: 71 percent / tetrahydrofuran; diethyl ether / 1.8 h / -78 - 0 °C 21: 95 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 22: 1.) sodium hydride / 1.) THF, RT, 1 h 2.) RT, overnight 23: 80 percent / 80percent aq CH3COOH / Ambient temperature 24: 77 percent / 1N aq NaHCO3, 1N aq KOH / ethanol; tetrahydrofuran / 4.5 h / 0 °C View Scheme

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

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

1: 43 percent / ethylaluminium dichloride / CH2Cl2; hexane / 12 h / Ambient temperature 2: 72 percent / iodine / tetrahydrofuran; H2O / 4 h / 0 - 20 °C 3: 82 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / Ambient temperature 4: 91 percent / lithium aluminium hydride / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C 5: pyridine / 2 h / 0 - 20 °C 6: 100 percent / xylene / 12 h / Heating 7: 90 percent / N-methylmorpholine N-oxide, OsO4 / acetone; H2O / 24 h / Ambient temperature 8: 94 percent / cupric sulfate, p-toluenesulfonic acid / 24 h / Ambient temperature 9: 74 percent / diisobutylaluminium hydride / diethyl ether; hexane / 0.5 h / -90 °C 10: 1.) Mg, 2.) zinc bromide / 1.) THF, RT, 1.5 h, 2.) CH2Cl2, -100 deg C, 1 h 11: 81 percent / dicyclohexylcarbodiimide (DCC), (dimethylamino)pyridine (DMAP) / CH2Cl2 / Ambient temperature 12: lithium diisopropylamide (LDA), trimethylsilyl chloride (TMSCl), pyridine / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C 13: diethyl ether / 0 °C 14: 77 percent / diisobutylaluminium hydride / CH2Cl2; hexane / 0.5 h / -20 °C 15: 60 percent / triphenylphosphine, imidazole, diisopropylamine, iodine / diethyl ether; acetonitrile / 3 h / Ambient temperature 16: 70 percent / azoisobutyronitrile, tributyltin hydride / aq. ethanol / 12 h / Ambient temperature 17: 70 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature 18: 97 percent / pyridinium chlorochromate, sodium acetate, Celite / CH2Cl2 / 1.5 h / Ambient temperature 19: 71 percent / tetrahydrofuran; diethyl ether / 1.8 h / -78 - 0 °C 20: 95 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 21: 1.) sodium hydride / 1.) THF, RT, 1 h 2.) RT, overnight 22: 80 percent / 80percent aq CH3COOH / Ambient temperature 23: 77 percent / 1N aq NaHCO3, 1N aq KOH / ethanol; tetrahydrofuran / 4.5 h / 0 °C View Scheme

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

1: 72 percent / iodine / tetrahydrofuran; H2O / 4 h / 0 - 20 °C 2: 82 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / tetrahydrofuran / Ambient temperature 3: 91 percent / lithium aluminium hydride / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C 4: pyridine / 2 h / 0 - 20 °C 5: 100 percent / xylene / 12 h / Heating 6: 90 percent / N-methylmorpholine N-oxide, OsO4 / acetone; H2O / 24 h / Ambient temperature 7: 94 percent / cupric sulfate, p-toluenesulfonic acid / 24 h / Ambient temperature 8: 74 percent / diisobutylaluminium hydride / diethyl ether; hexane / 0.5 h / -90 °C 9: 1.) Mg, 2.) zinc bromide / 1.) THF, RT, 1.5 h, 2.) CH2Cl2, -100 deg C, 1 h 10: 81 percent / dicyclohexylcarbodiimide (DCC), (dimethylamino)pyridine (DMAP) / CH2Cl2 / Ambient temperature 11: lithium diisopropylamide (LDA), trimethylsilyl chloride (TMSCl), pyridine / tetrahydrofuran; hexane / 1.25 h / -78 - 20 °C 12: diethyl ether / 0 °C 13: 77 percent / diisobutylaluminium hydride / CH2Cl2; hexane / 0.5 h / -20 °C 14: 60 percent / triphenylphosphine, imidazole, diisopropylamine, iodine / diethyl ether; acetonitrile / 3 h / Ambient temperature 15: 70 percent / azoisobutyronitrile, tributyltin hydride / aq. ethanol / 12 h / Ambient temperature 16: 70 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature 17: 97 percent / pyridinium chlorochromate, sodium acetate, Celite / CH2Cl2 / 1.5 h / Ambient temperature 18: 71 percent / tetrahydrofuran; diethyl ether / 1.8 h / -78 - 0 °C 19: 95 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 20: 1.) sodium hydride / 1.) THF, RT, 1 h 2.) RT, overnight 21: 80 percent / 80percent aq CH3COOH / Ambient temperature 22: 77 percent / 1N aq NaHCO3, 1N aq KOH / ethanol; tetrahydrofuran / 4.5 h / 0 °C View Scheme