1: 80 percent / methanol 2: 1) OsO4 2) LiAlH4 / 1) ether, rt, 5 weeks 2) ether, rt, overnight 3) ether, reflux, 3 h 3: 89 percent / CF3COOH / methanol; H2O / 4 h / Ambient temperature 4: 26 percent / NaIO4 / tetrahydrofuran; H2O / 2 h View Scheme

Multi-step reaction with 7 steps 1: 73 percent / 5 h / 220 °C2: 87 percent / hydrazine hydrate / ethanol; bis-(2-hydroxy-ethyl) ether / 72 h / Heating3: 69 percent / Et3N, S2Cl2 / petroleum ether / 4 h4: 83 percent / petroleum ether / 3 h / 0 °C5: 79 percent / 0.5 h / 140 °C6: 1.) (n-Bu)3P 2.) MeI / 1.) 140 deg C 2.) petroleum ether (60-70 deg C)7: 1) OsO4 2) LiAlH4 / 1) ether, pyridine, 12 days 2) ether, pyridine, rt, overnight 3) ether, pyridine, reflux, 3 h