1: LiAlH4 / diethyl ether 2: 70 percent / pyridine / CH2Cl2 / a) 0 deg C, 0.5 h; b) r.t., 8 h 3: 90 percent / LiAlH4 / diethyl ether / 4 h / Heating 4: 1) N,N-carbonyldiimidazole / 1) THF, r.t., 1 h; 2) r.t., 10 h 5: 93 percent / LiAlH4 / diethyl ether / 6 h / Heating View Scheme

<b>Multi-step reaction with 6 steps<br /> </b>1: 94 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature<br />2: 78 percent / pyridine / a) 0 deg C, 1.5 h; b) r.t., 6 h<br />3: 28 percent / dimethylformamide / 7 h / 70 &deg;C<br />4: 88 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature<br />5: 49 percent / pyridine / a) 0 deg C, 1.5 h; b) r.t., 6 h<br />6: NaN₃ / dimethylformamide<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: 90 percent / zinc powder, NaI, sodium acetate, acetic acid / CH₂Cl₂ / 4 h / Ambient temperature<br />2: 94 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature<br />3: 78 percent / pyridine / a) 0 deg C, 1.5 h; b) r.t., 6 h<br />4: 28 percent / dimethylformamide / 7 h / 70 &deg;C<br />5: 88 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature<br />6: 49 percent / pyridine / a) 0 deg C, 1.5 h; b) r.t., 6 h<br />7: NaN₃ / dimethylformamide<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 87 percent / zinc powder, NaI, sodium acetate, acetic acid / CH₂Cl₂ / 4 h / Ambient temperature<br />2: 88 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature<br />3: 49 percent / pyridine / a) 0 deg C, 1.5 h; b) r.t., 6 h<br />4: NaN₃ / dimethylformamide<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: 66 percent / m-CPBA, NaHCO₃ / CH₂Cl₂ / 0.5 h / 0 &deg;C<br />2: 1) O₃, 2) Me₂S / 1) methanol, -65 - -70 deg C; 2) -78 deg C to r.t., 4 h<br />3: 82 percent / m-CPBA / CH₂Cl₂ / 60 h<br />4: 87 percent / zinc powder, NaI, sodium acetate, acetic acid / CH₂Cl₂ / 4 h / Ambient temperature<br />5: 88 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature<br />6: 49 percent / pyridine / a) 0 deg C, 1.5 h; b) r.t., 6 h<br />7: NaN₃ / dimethylformamide<br /> <br /> &nbsp;