1: 1.) aq. 5 N NaOH / 1.) DMSO 2: 85 percent / tri-n-butyltin hydride, azobisisobutyronitrile / toluene / 1 h / Heating 3: 67 percent / 1 M tetra-n-butylammonium fluoride / tetrahydrofuran View Scheme

1: 1.) aq. 5 N NaOH / 1.) DMSO 2: 85 percent / tri-n-butyltin hydride, azobisisobutyronitrile / toluene / 1 h / Heating 3: 67 percent / 1 M tetra-n-butylammonium fluoride / tetrahydrofuran 4: 78 percent / H2 / 10percent Pd/C / ethanol; H2O / 6 h / 2585.7 Torr View Scheme

Multi-step reaction with 2 steps 1: 87 percent / NaH / tetrahydrofuran2: 82 percent / tris(trimethylsilyl)silane; azobisizobutyronitrile / benzene / 4 h / 80 °C