Multi-step reaction with 10 steps
1: 94 percent / H2, AcOH / 10percent Pd/C / ethyl acetate / 48 h
2: 86 percent / BF3 / CH2Cl2 / 2 h / Ambient temperature
3: K2CO3 / acetone / 84 h / Heating
4: 30.47 g / 4 h / 210 °C
5: 1.) O3, MeOH, 2,) PPh3 / 1.) CH2Cl2, -76 deg C, 5 min, 2.) CH2Cl2, MeOH, -76 deg C, 15 min
6: 90 percent / benzene / 28 h / Heating
7: 1.) NaH / 1.) THF, 0 deg C, 20 min, 2.) THF, from 0 deg C to RT, 1 h
8: 85 percent / NaBH4 / methanol / 1 h / 0 - 20 °C
9: 79 percent / N,N-diisopropylethylamine, CBr4, Ph3P / CH2Cl2 / 10.75 h / -76 - 20 °C
10: 1.) NaH / 1.) DMF 2.) DMF, RT, 12 h
With
methanol; sodium tetrahydroborate; carbon tetrabromide; boron trifluoride; hydrogen; sodium hydride; potassium carbonate; ozone; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine;
palladium on activated charcoal;
In
methanol; dichloromethane; ethyl acetate; acetone; benzene;
DOI:10.1021/jm9501339