Multi-step reaction with 15 steps
1: K2CO3 / acetone / 3 h / Heating
2: H2 / 10percent Pd/C / methanol; ethyl acetate / Ambient temperature
3: pyridine
4: 1.) AcOH, BF3(g), 2.) pyridine / 1.) from 50 to 60 deg C, 5 h
5: 10percent aq. NaOH / methanol / 0.25 h / Ambient temperature
6: (i-Pr)2NEt / CH2Cl2 / 0.83 h / 5 °C
7: pyridine / 3 h / 60 - 70 °C
8: KOH, pyridine / 2 h / 60 °C
9: conc. H2SO4, HOAc / 1 h / 50 °C
10: 97 percent / K2CO3 / dimethylformamide / 0.08 h / 150 °C
11: 1.) dimethyldioxirane, 2.) p-TsOH / 1.) CH2Cl2, Me2CO, 0 deg C, 12 h, 2.) CH2Cl2, 0 deg C, 30 min
12: 100 percent / K2CO3 / acetone / 2 h / Heating
13: 100 percent / AlBr3 / acetonitrile / 0.83 h / 0 °C
14: 100 percent / K2CO3 / methanol / 0.67 h / 70 °C
15: 100 percent / H2 / 10percent Pd/C / ethyl acetate; methanol / Ambient temperature
With
pyridine; potassium hydroxide; sodium hydroxide; aluminum tri-bromide; sulfuric acid; boron trifluoride; hydrogen; 3,3-dimethyldioxirane; potassium carbonate; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine;
palladium on activated charcoal;
In
methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1246/bcsj.69.1033