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