1: 1.) tributylborane, sodium borohydride, 2.) 3 N NaOH, 30percent H2O2 / 1.) THF, a) RT, b) 0 deg C, 3 h, 2.) RT 2: toluene / 6 h / Heating View Scheme

Multi-step reaction with 2 steps 1: 1.) tributylborane, sodium borohydride, 2.) 3 N NaOH, 30percent H2O2 / 1.) THF, a) RT, b) 0 deg C, 3 h, 2.) RT2: toluene / 6 h / Heating  

Multi-step reaction with 4 steps 1: NaOH / methanol; H2O / 2 h / Heating2: 43 percent / acetic anhydride / 4 h / 90 °C3: 1.) concd. HCl, 2.) p-TSA, H2O / 1.) ethanol, reflux, 24 h, 2.) acetone, reflux, 2 d4: 1.) sodium hydride, n-butyllithium / 1.) THF, hexane, 0 deg C, 30 min, 2.)a) -78 deg C, 30 min, b) 0 deg C, 1 h  

Multi-step reaction with 3 steps 1: 43 percent / acetic anhydride / 4 h / 90 °C2: 1.) concd. HCl, 2.) p-TSA, H2O / 1.) ethanol, reflux, 24 h, 2.) acetone, reflux, 2 d3: 1.) sodium hydride, n-butyllithium / 1.) THF, hexane, 0 deg C, 30 min, 2.)a) -78 deg C, 30 min, b) 0 deg C, 1 h  

Multi-step reaction with 2 steps 1: 1.) concd. HCl, 2.) p-TSA, H2O / 1.) ethanol, reflux, 24 h, 2.) acetone, reflux, 2 d2: 1.) sodium hydride, n-butyllithium / 1.) THF, hexane, 0 deg C, 30 min, 2.)a) -78 deg C, 30 min, b) 0 deg C, 1 h