1: 43 percent / pyridine / diethyl ether / 12 h / Ambient temperature; 1) 5 deg C, 1 h 2) room temperature 12 h 2: CuI, 2,2'-bipyridyl / 2 deg C, 2 h, THF View Scheme

1: triethylamine / CH2Cl2 / 1) 0 deg C, 0.5 h, 2) RT, 6 h 2: LiBr / acetone / 5 h / Ambient temperature 3: 86 percent / dimethylsulfoxide / Ambient temperature 4: KOH / ethane-1,2-diol / 6 h / Heating 6: 90 percent / lithium aluminium hydride / diethyl ether / 3 h / Ambient temperature 7: 74 percent / pyridine / 24 h / Ambient temperature View Scheme

1: 95 percent / triethylamine / CH2Cl2 / 0 °C 2: 90 percent / NaI / acetone / 5 h / Heating View Scheme

Dess-Martin periodane in dichloromethane T=20°C; 1.5 h;

1: triethylamine / CH2Cl2 / 1) 0 deg C, 0.5 h, 2) RT, 6 h 2: LiBr / acetone / 5 h / Ambient temperature 3: 86 percent / dimethylsulfoxide / Ambient temperature 4: KOH / ethane-1,2-diol / 6 h / Heating 6: 90 percent / lithium aluminium hydride / diethyl ether / 3 h / Ambient temperature View Scheme

<b>Multi-step reaction with 2 steps<br /> </b>1: LiNH₂ / liquid ammonia; tetrahydrofuran<br />2: 95 percent / H₂, quinoline / Pd-BaCO₃ (Lindlar catalyst) / hexane / 735.5 Torr<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: Li₂CuCl₄ / 1) THF -78 deg C, 2 hours 2) room temperature 15 h<br />2: 11.7 g / 5percent aq. HCl / acetone / 6 h / Ambient temperature<br />3: diisobutylaluminum hydride / diethyl ether / 1.5 h / -10 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 99.5 percent / pyridine / 15 h / -10 &deg;C<br />2: Li₂CuCl₄ / 1) THF -78 deg C, 2 hours 2) room temperature 15 h<br />3: 11.7 g / 5percent aq. HCl / acetone / 6 h / Ambient temperature<br />4: diisobutylaluminum hydride / diethyl ether / 1.5 h / -10 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: LiNH₂ / liquid ammonia; tetrahydrofuran<br />2: 95 percent / H₂, quinoline / Pd-BaCO₃ (Lindlar catalyst) / hexane / 735.5 Torr<br /> <br /> &nbsp;