1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 2: 73 percent / quinoline; hydrogen / palladium on BaSO4 / ethyl acetate / 3 h / 20 °C / 750.06 Torr 3: 82 percent / triethylamine / CH2Cl2 / 0 - 20 °C 4: 78 percent / bis(tricyclohexylphosphine) benzylidene Ru(IV) dichloride / CH2Cl2 / 6 h / Heating View Scheme

<b>Multi-step reaction with 3 steps<br /> </b>1.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / -25 - -15 &deg;C<br />2.1: 71 percent / diisobutylaluminium hydride / CH₂Cl₂ / 3.5 h / -78 &deg;C<br />3.1: LDA / tetrahydrofuran; diethyl ether / 0.5 h / -78 &deg;C<br />3.2: 87 percent / tetrahydrofuran; diethyl ether / 3 h / -78 - 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1.1: 71 percent / diisobutylaluminium hydride / CH₂Cl₂ / 3.5 h / -78 &deg;C<br />2.1: LDA / tetrahydrofuran; diethyl ether / 0.5 h / -78 &deg;C<br />2.2: 87 percent / tetrahydrofuran; diethyl ether / 3 h / -78 - 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1.1: N,N'-carbonyldiimidazole / tetrahydrofuran / 8 h / 20 &deg;C<br />1.2: 62 percent / tetrahydrofuran / 36 h / 20 &deg;C<br />2.1: 96 percent / hydrogen / [RuBr₂((R)-SYNPHOS)] / 0.5 h / 50 &deg;C / 7500.6 Torr<br />3.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / -25 - -15 &deg;C<br />4.1: 71 percent / diisobutylaluminium hydride / CH₂Cl₂ / 3.5 h / -78 &deg;C<br />5.1: LDA / tetrahydrofuran; diethyl ether / 0.5 h / -78 &deg;C<br />5.2: 87 percent / tetrahydrofuran; diethyl ether / 3 h / -78 - 0 &deg;C<br /> <br /> &nbsp;