1: 87 percent / C5H5NHBr3 / tetrahydrofuran / 1.) 0 deg C, 30 min; 2.) rt, 2.5 h 2: 72 percent / NaNH2 / liquid ammonia; diethyl ether / 1.) -50 deg C, 30 min; 2.) -27 deg C, 3.5 h 3: 1) n-BuLi / 1) hexane, THF, -5 deg C, 45 min; 2) THF, -60 deg C, 1 h, then room temp. 4: 1) NaOH / 1) MeOH, room temp., 30 min; 2) MeOH, room temp., 4 h 5: 1) CuI / 1) THF, -65 deg C, 15 min; 2) THF, -65 deg C, 3 h 6: 90 percent / LiAlH4 / diethyl ether / 3 h / 0 °C View Scheme

<b>Multi-step reaction with 3 steps<br /> </b>1: p-TsOH / acetone / 0.5 h / Ambient temperature<br />2: (n-Bu)3P / tetrahydrofuran / 3.5 h / Ambient temperature<br />3: 81 percent / 35percent aq. H₂O₂ / tetrahydrofuran / 1.) -5 deg C, 1 h; 2.) rt, 1.5 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: LiAlH₄ / tetrahydrofuran / 30 min at 0 deg C, then 1 h at room temp., then 30 min reflux<br />2: p-TsOH / acetone / 0.5 h / Ambient temperature<br />3: (n-Bu)3P / tetrahydrofuran / 3.5 h / Ambient temperature<br />4: 81 percent / 35percent aq. H₂O₂ / tetrahydrofuran / 1.) -5 deg C, 1 h; 2.) rt, 1.5 h<br /> <br /> &nbsp;