Multi-step reaction with 10 steps
1: tetrahydrofuran; diethyl ether / 0.25 h
2: 99 percent / H2 / 10percent Pd/C / methanol / 3 h
3: Ph3P / toluene / 22 h / Ambient temperature
4: 1.) MeMgCl / 1.) toluene, THF, Et2O, -78 deg C, 2.) toluene, -78 deg C, 1.5 h
5: 1.) SO2Cl2, 2.) H2O / 1.) CH2Cl2, -5 deg C, 10 min, 2.) acetone, 15 min
6: aq. KMnO4 / acetone / 3 h / Ambient temperature
7: 75 percent / K2CO3 / dimethylformamide / 12 h / Ambient temperature
8: 100 percent / NaBH4 / tetrahydrofuran / 0.08 h / -5 - 20 °C
9: DMAP / CH2Cl2 / 0.25 h
10: 45 percent / 0.08 h / 200 °C
With
dmap; sodium tetrahydroborate; potassium permanganate; sulfuryl dichloride; water; hydrogen; methylmagnesium chloride; potassium carbonate; triphenylphosphine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1039/a700655a