(i) NaN3, H2SO4, (ii) aq. NH3; Multistep reaction;

1: conc. H2SO4 / 8 h / Heating 2: 86 percent / LiAlH4 / diethyl ether / 1 h / Ambient temperature 3: 90 percent / pyridinium dichromate / CH2Cl2 / 0.17 h 4: 67 percent / 80percent hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 3 h / Heating 5: 1.) t-butyllithium, Cu2Br2-Me2S, 2.) O2 / 1.) hexane, THF, -78 deg C, 1 h, 2.) from -78 deg C to RT, 1 h View Scheme

1: conc. H2SO4 / 8 h / Heating 2: 86 percent / LiAlH4 / diethyl ether / 1 h / Ambient temperature 3: 90 percent / pyridinium dichromate / CH2Cl2 / 0.17 h 4: 67 percent / 80percent hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 3 h / Heating 5: 1.) t-butyllithium, Cu2Br2-Me2S, 2.) O2 / 1.) hexane, THF, -78 deg C, 1 h, 2.) from -78 deg C to RT, 1 h View Scheme

sulfuric acid Heating;

1: conc. H2SO4 / 8 h / Heating 2: 86 percent / LiAlH4 / diethyl ether / 1 h / Ambient temperature 3: 90 percent / pyridinium dichromate / CH2Cl2 / 0.17 h 4: 67 percent / 80percent hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 3 h / Heating 5: 1.) t-butyllithium, Cu2Br2-Me2S, 2.) O2 / 1.) hexane, THF, -78 deg C, 1 h, 2.) from -78 deg C to RT, 1 h View Scheme