1.1: In / tetrahydrofuran / Heating 1.2: (+)-cinchonine / tetrahydrofuran / 20 °C 1.3: 87 percent / tetrahydrofuran / 2 h / -78 °C 2.1: 98 percent / imidazole / dimethylformamide / 6 h / 20 °C 3.1: O3 / methanol / -78 °C 3.2: Me2S / methanol / 12 h / -78 - 20 °C 4.1: 1.01 g / H2 / Pd(OH)2/C / ethanol / 10 h / 20 °C 5.1: 90 percent / aq. K2CO3 / CH2Cl2 / 0.5 h / 20 °C 6.1: 93 percent / Dowex 50W-X8 / aq. methanol / 18 h / 20 °C 7.1: 99 percent / imidazole / CH2Cl2 / 1 h / 20 °C 8.1: 92 percent / Et3N / tetrahydrofuran / 0.33 h / 20 °C 9.1: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 10.1: 65 percent / NaOAc; H2 / Pd/C / methanol / 6 h / 60 °C 11.1: 92 percent / Dowex 50W-X8; H2O / tetrahydrofuran / Heating View Scheme

<b>Multi-step reaction with 4 steps<br /> </b>1: H₂ / 10percent Pd/C / ethyl acetate / 24 h / 760 Torr<br />2: Pb(NO₃)2, Et₃N / CH₂Cl₂ / 48 h / Ambient temperature<br />3: 94 percent / DIBAL / toluene / 0.5 h / -78 &deg;C<br />4: 1) N-chlorosuccinimide, Me₂S, 2) NEt₃ / 1) toluene, -25 deg C, 5.5 h, 2) 20 min.<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: Pb(NO₃)2, Et₃N / CH₂Cl₂ / 48 h / Ambient temperature<br />2: 94 percent / DIBAL / toluene / 0.5 h / -78 &deg;C<br />3: 1) N-chlorosuccinimide, Me₂S, 2) NEt₃ / 1) toluene, -25 deg C, 5.5 h, 2) 20 min.<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 94 percent / DIBAL / toluene / 0.5 h / -78 &deg;C<br />2: 1) N-chlorosuccinimide, Me₂S, 2) NEt₃ / 1) toluene, -25 deg C, 5.5 h, 2) 20 min.<br /> <br /> &nbsp;