1: 93 percent / sodium borohydride, 37percent hydrochloric acid / methanol; H2O / 2 h / 0 °C 2: 85 percent / pyridine / 15 h / Ambient temperature 3: 86 percent / ferric chloride on silica gel / CHCl3 / 15 h / Ambient temperature 4: sodium periodate / methanol; H2O / 12 h / Ambient temperature 5: NaBH4 / methanol; H2O / 0.5 h / Ambient temperature 6: 91 percent / pyridine, 4-dimethylaminopyridine / 12 h / Ambient temperature 7: 82 percent / hydrogen / 10percent Pd/C / ethyl acetate / 5 h / Ambient temperature 8: 99 percent / dimethyl sulfoxide, oxalyl chloride / CH2Cl2 / 0.25 h / -78 °C 9: zinc powder, acetic acid / tetrahydrofuran; H2O / 30 h / Ambient temperature 10: zinc chloride / CH2Cl2 / 0.17 h / Ambient temperature 11: 81 percent / trifluoroacetic acid / CH2Cl2 / 5 h / Ambient temperature 12: 68 percent / N,N-diisopropylethylamine / acetonitrile / 3 h / 60 °C 13: 79 percent / 2.6 M Jones reagent, celite / acetone / 0.5 h / Ambient temperature 14: 88 percent / sodium hydroxide / methanol / 2 h / Ambient temperature 15: 81 percent / silver nitrate / methanol / 1 h / Ambient temperature View Scheme