1: 97 percent / I2, Ph3P, imidazole / CH2Cl2; benzene / 1 h 2: 91 percent / tetrahydrofuran / 12 h / 0 °C 3: 100 percent / (DHQD)2AQN, K2Fe3(CN)6, K2CO3, K2OsO2(OH)4 / 2-methyl-propan-2-ol; H2O / 12 h / 0 °C 4: 19 percent / pyridine / 10 h / Ambient temperature 5: 79 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature 6: 1.) BF3*OEt2 / 1.) THF, -78 deg C, 10 min, 2.) THF, 20 min 7: i-Pr2NEt / CH2Cl2 / 12 h / Ambient temperature 8: TBAF / tetrahydrofuran / 6 h / 40 °C 9: 2,6-lutidine / tetrahydrofuran / 0.33 h 10: 1.) Pd(PPh3)4, H2O, 2.) AgNO3/SiO2 / 1.) THF, 1.7 h, 2.) CH2Cl2, hexane, 2 h 11: 67 percent / PPTS / ethanol / 16 h / 40 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587189', constants.ctx, '0')">hydrogen</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '19211235', constants.ctx, '0')">rhodium on alumina</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '506104', constants.ctx, '0')">ethyl acetate</a> <br />12&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 86 percent / LiBEt₃H / tetrahydrofuran / 12 h / 0 &deg;C<br />2: 98 percent / H₂ / Rh-Al₂O₃ / ethyl acetate / 12 h<br /> <br /> &nbsp;