1: 95 percent / NaH / tetrahydrofuran / -30 °C 2: 87 percent / NH3 / methanol 3: 90 percent / n-Bu3N, PPh3 / Pd(OAc)2 / toluene / 48 h / 110 °C / 3800 Torr 4: 65 percent / HCl / methanol / 12 h / 50 °C 5: molecular sieve, PCC / CH2Cl2 / 2 h / Ambient temperature 6: 1.) t-BuOK / 1.) THF, 20 min; 2.) THF, room temperature, 1 h 7: 30 percent / MCPBA, NaHCO3 / not given 8: 1.) Li, ClPPh2 / 1.) THF; 2.) THF 9: 1.) NaBH4; 2.) silica gel / 1.) EtOH, 0 degC, 3 h; 2.) room temperature, 30 min, benzene View Scheme

Multi-step reaction with 2 steps 1: 95 percent / NaH / tetrahydrofuran / -30 °C2: 87 percent / NH3 / methanol  

Multi-step reaction with 3 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 Torr  

Multi-step reaction with 6 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 h  

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: 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: 18 percent / N-methylmorpholine-N-oxide monohydrate, OsO4 / CH2Cl2; acetone; 2-methyl-propan-2-ol; H2O / 6 h  

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: 18 percent / N-methylmorpholine-N-oxide monohydrate, OsO4 / CH2Cl2; acetone; 2-methyl-propan-2-ol; H2O / 6 h8: Et3N / CH2Cl2 / 0.08 h / 0 °C