sodium tetrahydroborate; silica gel 1.) EtOH, 0 degC, 3 h; 2.) room temperature, 30 min, benzene; Yield given. Multistep reaction;

Multi-step reaction with 6 steps 1: 90 percent / n-Bu3N, PPh3 / Pd(OAc)2 / toluene / 48 h / 110 °C / 3800 Torr2: 65 percent / HCl / methanol / 12 h / 50 °C3: molecular sieve, PCC / CH2Cl2 / 2 h / Ambient temperature4: 1.) t-BuOK / 1.) THF, 20 min; 2.) THF, room temperature, 1 h5: 30 percent / MCPBA, NaHCO3 / not given6: 1.) Li, ClPPh2 / 1.) THF; 2.) THF  

Multi-step reaction with 9 steps 1: 92 percent / diisopropylethylamine / CH2Cl2 / Ambient temperature2: 95 percent / NaH / tetrahydrofuran / -30 °C3: 87 percent / NH3 / methanol4: 90 percent / n-Bu3N, PPh3 / Pd(OAc)2 / toluene / 48 h / 110 °C / 3800 Torr5: 65 percent / HCl / methanol / 12 h / 50 °C6: molecular sieve, PCC / CH2Cl2 / 2 h / Ambient temperature7: 1.) t-BuOK / 1.) THF, 20 min; 2.) THF, room temperature, 1 h8: 30 percent / MCPBA, NaHCO3 / not given9: 1.) Li, ClPPh2 / 1.) THF; 2.) THF  

Multi-step reaction with 8 steps 1: 95 percent / NaH / tetrahydrofuran / -30 °C2: 87 percent / NH3 / methanol3: 90 percent / n-Bu3N, PPh3 / Pd(OAc)2 / toluene / 48 h / 110 °C / 3800 Torr4: 65 percent / HCl / methanol / 12 h / 50 °C5: molecular sieve, PCC / CH2Cl2 / 2 h / Ambient temperature6: 1.) t-BuOK / 1.) THF, 20 min; 2.) THF, room temperature, 1 h7: 30 percent / MCPBA, NaHCO3 / not given8: 1.) Li, ClPPh2 / 1.) THF; 2.) THF  

Multi-step reaction with 7 steps 1: 87 percent / NH3 / methanol2: 90 percent / n-Bu3N, PPh3 / Pd(OAc)2 / toluene / 48 h / 110 °C / 3800 Torr3: 65 percent / HCl / methanol / 12 h / 50 °C4: molecular sieve, PCC / CH2Cl2 / 2 h / Ambient temperature5: 1.) t-BuOK / 1.) THF, 20 min; 2.) THF, room temperature, 1 h6: 30 percent / MCPBA, NaHCO3 / not given7: 1.) Li, ClPPh2 / 1.) THF; 2.) THF