Multi-step reaction with 10 steps
1: 1) 1.56 M nBuLi in hexane / 1) THF, -40 deg C then 0 deg C, 40 min, 2) THF, HMPA, 0 deg C, 1 h then 1 h, RT
2: 96 percent / hydrogen / 10percent Pd/C / ethyl acetate / 12 h / Ambient temperature
3: pyridine / ) deg C, 1 h; RT, 5 h
4: 91 percent / NaI, NaHCO3 / acetone / 8 h
5: 10 0.6 m NaHMDS in toluene / 1) THF, 0 deg C, 30 min, 2) THF, toluene, HMPA, 0 deg C to RT
6: 99 percent / p-TsOH / methanol / 48 h
7: pyridine / 0 deg C, 1 h; RT, 5 h
8: KOH (powdered) / tetrahydrofuran / 2 h / 0 °C
9: 1) 1.6 m nBuLi in hexane, 2) BF3*Et2O / 1) THF, -78 deg C, 30 min, 2) THF, hexane, 20 min, -78 deg C, 3) THF, hexane, ether, 1 h, -78 deg C
10: 92 percent / hydrogen / (triphenylphosphine)rhodium / benzene / 5 h
With
pyridine; potassium hydroxide; n-butyllithium; boron trifluoride diethyl etherate; hydrogen; sodium hexamethyldisilazane; sodium hydrogencarbonate; toluene-4-sulfonic acid; sodium iodide;
palladium on activated charcoal; (triphenylphosphine)rhodium;
In
tetrahydrofuran; methanol; ethyl acetate; acetone; benzene;