1.1: 89 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - -50 °C 2.1: (c-Hex)2BOTf; triethylamine / CH2Cl2 / 2.5 h / -78 °C 2.2: CH2Cl2 / 3 h / -78 °C 2.3: 92 percent / H2O2 / CH2Cl2; methanol; H2O / -78 - 20 °C / pH 7 3.1: LiOH*H2O / tetrahydrofuran; H2O / 7 h / 0 - 20 °C 4.1: 0.217 g / benzene; methanol; hexane / 2 h / 20 °C 5.1: 95 percent / 2,6-lutidine / CH2Cl2 / 0 - 20 °C 6.1: DIBAL-H / CH2Cl2 / 1.75 h / -78 °C 7.1: 0.190 g / KHMDS; 18-crown-6 / tetrahydrofuran; toluene / 4 h / -78 °C 8.1: 91 percent / DIBAL-H / diethyl ether; toluene / 1 h / -78 °C 9.1: 89 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 0 °C 10.1: 93 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 2 h / 0 °C 11.1: 82 percent / sodium borohydride; sulfur / tetrahydrofuran / 2 h / 65 °C 12.1: 85 percent / morpholine; tetrakis(triphenylphosphine)palladium(0) / tetrahydrofuran / 24 h 13.1: 78 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; diisopropylethylamine / toluene / 16.5 h / 85 °C 14.1: 90 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 4.5 h / 0 - 20 °C 15.1: 95 percent / aq. HF / acetonitrile / 6 h / 20 °C 16.1: 5 percent / aq. HNO3; acetic acid / 0.02 h / 20 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4123663', constants.ctx, '0')">diisobutylaluminium hydride</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, '635760', constants.ctx, '0')">toluene</a> <br />T=-78&deg;C;&nbsp;4&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 15 steps<br /> </b>1.1: 91 percent / proton sponge / CH₂Cl₂ / 8 h / 20 &deg;C<br />2.1: 89 percent / methanol; tetrahydrofuran / 2.5 h / 0 &deg;C<br />3.1: 95 percent / ceric ammonium nitrate (CAN); H₂O / acetonitrile / 0.5 h / 0 &deg;C<br />4.1: 99 percent / imidazole / dimethylformamide / 18 h / 20 &deg;C<br />5.1: 90 percent / DIBAL-H / CH₂Cl₂; toluene / 3 h / -78 &deg;C<br />6.1: 80 percent / CH₂Cl₂ / 2.5 h / -78 &deg;C<br />7.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 &deg;C<br />8.1: NaHMDS / diethyl ether / 1 h / 0 - 20 &deg;C<br />8.2: 98 percent / diethyl ether / 2 h / 20 &deg;C<br />9.1: 99 percent / aq. HF / acetonitrile / 3 h / 20 &deg;C<br />10.1: BH₃*THF / tetrahydrofuran / 2.25 h / -5 &deg;C<br />10.2: 78 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran; methanol / 2 h / 0 - 20 &deg;C<br />11.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 &deg;C<br />12.1: 80 percent / CSA / methanol; CH₂Cl₂ / 2.5 h / 0 &deg;C<br />13.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 0 &deg;C<br />14.1: 93 percent / toluene / 7 h / 90 &deg;C<br />15.1: 86 percent / DIBAL-H / tetrahydrofuran; toluene / 4 h / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 14 steps<br /> </b>1.1: 89 percent / methanol; tetrahydrofuran / 2.5 h / 0 &deg;C<br />2.1: 95 percent / ceric ammonium nitrate (CAN); H₂O / acetonitrile / 0.5 h / 0 &deg;C<br />3.1: 99 percent / imidazole / dimethylformamide / 18 h / 20 &deg;C<br />4.1: 90 percent / DIBAL-H / CH₂Cl₂; toluene / 3 h / -78 &deg;C<br />5.1: 80 percent / CH₂Cl₂ / 2.5 h / -78 &deg;C<br />6.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 &deg;C<br />7.1: NaHMDS / diethyl ether / 1 h / 0 - 20 &deg;C<br />7.2: 98 percent / diethyl ether / 2 h / 20 &deg;C<br />8.1: 99 percent / aq. HF / acetonitrile / 3 h / 20 &deg;C<br />9.1: BH₃*THF / tetrahydrofuran / 2.25 h / -5 &deg;C<br />9.2: 78 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran; methanol / 2 h / 0 - 20 &deg;C<br />10.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 &deg;C<br />11.1: 80 percent / CSA / methanol; CH₂Cl₂ / 2.5 h / 0 &deg;C<br />12.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 0 &deg;C<br />13.1: 93 percent / toluene / 7 h / 90 &deg;C<br />14.1: 86 percent / DIBAL-H / tetrahydrofuran; toluene / 4 h / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1.1: BH₃*THF / tetrahydrofuran / 2.25 h / -5 &deg;C<br />1.2: 78 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran; methanol / 2 h / 0 - 20 &deg;C<br />2.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 &deg;C<br />3.1: 80 percent / CSA / methanol; CH₂Cl₂ / 2.5 h / 0 &deg;C<br />4.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 0 &deg;C<br />5.1: 93 percent / toluene / 7 h / 90 &deg;C<br />6.1: 86 percent / DIBAL-H / tetrahydrofuran; toluene / 4 h / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 8 steps<br /> </b>1.1: NaHMDS / diethyl ether / 1 h / 0 - 20 &deg;C<br />1.2: 98 percent / diethyl ether / 2 h / 20 &deg;C<br />2.1: 99 percent / aq. HF / acetonitrile / 3 h / 20 &deg;C<br />3.1: BH₃*THF / tetrahydrofuran / 2.25 h / -5 &deg;C<br />3.2: 78 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran; methanol / 2 h / 0 - 20 &deg;C<br />4.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 &deg;C<br />5.1: 80 percent / CSA / methanol; CH₂Cl₂ / 2.5 h / 0 &deg;C<br />6.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 0 &deg;C<br />7.1: 93 percent / toluene / 7 h / 90 &deg;C<br />8.1: 86 percent / DIBAL-H / tetrahydrofuran; toluene / 4 h / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 9 steps<br /> </b>1.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 &deg;C<br />2.1: NaHMDS / diethyl ether / 1 h / 0 - 20 &deg;C<br />2.2: 98 percent / diethyl ether / 2 h / 20 &deg;C<br />3.1: 99 percent / aq. HF / acetonitrile / 3 h / 20 &deg;C<br />4.1: BH₃*THF / tetrahydrofuran / 2.25 h / -5 &deg;C<br />4.2: 78 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran; methanol / 2 h / 0 - 20 &deg;C<br />5.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 &deg;C<br />6.1: 80 percent / CSA / methanol; CH₂Cl₂ / 2.5 h / 0 &deg;C<br />7.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 0 &deg;C<br />8.1: 93 percent / toluene / 7 h / 90 &deg;C<br />9.1: 86 percent / DIBAL-H / tetrahydrofuran; toluene / 4 h / -78 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 11 steps<br /> </b>1.1: 90 percent / DIBAL-H / CH₂Cl₂; toluene / 3 h / -78 &deg;C<br />2.1: 80 percent / CH₂Cl₂ / 2.5 h / -78 &deg;C<br />3.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 &deg;C<br />4.1: NaHMDS / diethyl ether / 1 h / 0 - 20 &deg;C<br />4.2: 98 percent / diethyl ether / 2 h / 20 &deg;C<br />5.1: 99 percent / aq. HF / acetonitrile / 3 h / 20 &deg;C<br />6.1: BH₃*THF / tetrahydrofuran / 2.25 h / -5 &deg;C<br />6.2: 78 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran; methanol / 2 h / 0 - 20 &deg;C<br />7.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 &deg;C<br />8.1: 80 percent / CSA / methanol; CH₂Cl₂ / 2.5 h / 0 &deg;C<br />9.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 0 &deg;C<br />10.1: 93 percent / toluene / 7 h / 90 &deg;C<br />11.1: 86 percent / DIBAL-H / tetrahydrofuran; toluene / 4 h / -78 &deg;C<br /> <br /> &nbsp;