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

1: 1.) Mg, 2.) zinc bromide / 1.) THF, RT, 1.5 h, 2.) CH2Cl2, -100 deg C, 1 h 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: Et3N, DMAP / CH2Cl2 2: NaH / tetrahydrofuran / 12 h 3: O3, pyridine / CH2Cl2 5: 76 percent / PDC, 3 Angstroem molecular sieves / CH2Cl2 6: 1.) CeI3 / 1.) THF, from -100 deg C to 0 deg C, 30 min, 2.) THF 7: 75 percent / CBr4, BaCO3, Ph3P / CH2Cl2 / 0.75 h 8: 82 percent / n-Bu3SnH, AIBN / toluene / 1 h / 65 °C 9: 98 percent / PPTs / methanol / 14 h / 22 °C 10: MnO2 / tetrahydrofuran / 5 h 11: NaCN / acetic acid / 16 h View Scheme

1: 1.) TsCl, DMAP, Et3N, 2.) TsOH, NaOCH3 / 1.) CH2Cl2, 22 deg C, 4 h, 2.) MeOH, 22 deg C, 16 h 2: Et3N, DMAP / CH2Cl2 3: NaH / tetrahydrofuran / 12 h 4: O3, pyridine / CH2Cl2 6: 76 percent / PDC, 3 Angstroem molecular sieves / CH2Cl2 7: 1.) CeI3 / 1.) THF, from -100 deg C to 0 deg C, 30 min, 2.) THF 8: 75 percent / CBr4, BaCO3, Ph3P / CH2Cl2 / 0.75 h 9: 82 percent / n-Bu3SnH, AIBN / toluene / 1 h / 65 °C 10: 98 percent / PPTs / methanol / 14 h / 22 °C 11: MnO2 / tetrahydrofuran / 5 h 12: NaCN / acetic acid / 16 h View Scheme

1: 85 percent / LiAlH4 / diethyl ether / 1 h / 0 - 22 °C 2: 1.) TsCl, DMAP, Et3N, 2.) TsOH, NaOCH3 / 1.) CH2Cl2, 22 deg C, 4 h, 2.) MeOH, 22 deg C, 16 h 3: Et3N, DMAP / CH2Cl2 4: NaH / tetrahydrofuran / 12 h 5: O3, pyridine / CH2Cl2 7: 76 percent / PDC, 3 Angstroem molecular sieves / CH2Cl2 8: 1.) CeI3 / 1.) THF, from -100 deg C to 0 deg C, 30 min, 2.) THF 9: 75 percent / CBr4, BaCO3, Ph3P / CH2Cl2 / 0.75 h 10: 82 percent / n-Bu3SnH, AIBN / toluene / 1 h / 65 °C 11: 98 percent / PPTs / methanol / 14 h / 22 °C 12: MnO2 / tetrahydrofuran / 5 h 13: NaCN / acetic acid / 16 h View Scheme

1: 1.) CeI3 / 1.) THF, from -100 deg C to 0 deg C, 30 min, 2.) THF 2: 75 percent / CBr4, BaCO3, Ph3P / CH2Cl2 / 0.75 h 3: 82 percent / n-Bu3SnH, AIBN / toluene / 1 h / 65 °C 4: 98 percent / PPTs / methanol / 14 h / 22 °C 5: MnO2 / tetrahydrofuran / 5 h 6: NaCN / acetic acid / 16 h View Scheme

2: 76 percent / PDC, 3 Angstroem molecular sieves / CH2Cl2 3: 1.) CeI3 / 1.) THF, from -100 deg C to 0 deg C, 30 min, 2.) THF 4: 75 percent / CBr4, BaCO3, Ph3P / CH2Cl2 / 0.75 h 5: 82 percent / n-Bu3SnH, AIBN / toluene / 1 h / 65 °C 6: 98 percent / PPTs / methanol / 14 h / 22 °C 7: MnO2 / tetrahydrofuran / 5 h 8: NaCN / acetic acid / 16 h View Scheme

1: NaCN / acetic acid / 16 h View Scheme

1: O3, pyridine / CH2Cl2 3: 76 percent / PDC, 3 Angstroem molecular sieves / CH2Cl2 4: 1.) CeI3 / 1.) THF, from -100 deg C to 0 deg C, 30 min, 2.) THF 5: 75 percent / CBr4, BaCO3, Ph3P / CH2Cl2 / 0.75 h 6: 82 percent / n-Bu3SnH, AIBN / toluene / 1 h / 65 °C 7: 98 percent / PPTs / methanol / 14 h / 22 °C 8: MnO2 / tetrahydrofuran / 5 h 9: NaCN / acetic acid / 16 h View Scheme

1: MnO2 / tetrahydrofuran / 5 h 2: NaCN / acetic acid / 16 h View Scheme