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

Multi-step reaction with 2 steps 1: 100 percent / xylene / 12 h / Heating2: 90 percent / N-methylmorpholine N-oxide, OsO4 / acetone; H2O / 24 h / Ambient temperature