1: 49 percent / SeO2; aq. AcOH; t-BuOOH / CH2Cl2; decane / 2 h / 20 °C 2: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C 3: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C 4: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C 5: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C 6: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C 7: NaBH4 / methanol / 5 h / 20 °C 8: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating 9: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C 10: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 11: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 12: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 13: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 14: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 15: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 16: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme

Stage #1: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '103853', constants.ctx, '0')">1H-imidazole</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587194', constants.ctx, '0')">iodine</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '610776', constants.ctx, '0')">triphenylphosphine</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=0&deg;C;&nbsp;3&nbsp;h;&nbsp;<br />Stage #2: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3556712', constants.ctx, '0')">potassium <i>tert</i>-butylate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '506008', constants.ctx, '0')">dimethyl sulfoxide</a> <br />T=20&deg;C;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1.1: 98 percent / KH / tetrahydrofuran / Heating<br />2.1: 76 percent / Hoveyda-Grubbs catalyst / toluene / 30 h / Heating<br />3.1: aq. HCl / tetrahydrofuran / 3 h / Heating<br />4.1: 1.9 g / NaBH₄ / ethanol; tetrahydrofuran / 0.25 h / 0 &deg;C<br />5.1: PPh₃; imidazole; I₂ / tetrahydrofuran / 3 h / 0 &deg;C<br />5.2: 94 percent / t-BuOK / tetrahydrofuran; dimethylsulfoxide / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1.1: aq. HCl / tetrahydrofuran / 3 h / Heating<br />2.1: 1.9 g / NaBH₄ / ethanol; tetrahydrofuran / 0.25 h / 0 &deg;C<br />3.1: PPh₃; imidazole; I₂ / tetrahydrofuran / 3 h / 0 &deg;C<br />3.2: 94 percent / t-BuOK / tetrahydrofuran; dimethylsulfoxide / 20 &deg;C<br /> <br /> &nbsp;