Multi-step reaction with 12 steps
1: 93 percent / TsOH / toluene; dimethylformamide / 9 h / Heating
2: 183 g / KOH / 0.5 h / 120 °C
3: 85 percent / AcOH / H2O / 1.5 h / 80 - 100 °C
4: 1.) Bu2SnO / 1.) toluene, 110 deg C; 2.) DMF, 80 deg C
5: NaH / dimethylformamide / 4 h / 40 °C
6: TsOH / 5percent Pd/C / aq. ethanol / 22 h / Heating
7: 72 percent / pyridinium chlorochromate / CH2Cl2 / 24 h / 25 °C
8: 25 percent / BuLi / tetrahydrofuran / 0.75 h / 0 - 21 °C
9: 24 percent / BF3*Et2O / diethyl ether / 1.5 h / Heating
10: 92 percent / NaBH4 / ethanol / 0.42 h / Ambient temperature
11: 100 percent / pyridine / DMAP / CH2Cl2 / 2 h / Ambient temperature
12: 25 percent / hydrogen / 5percent Pd/C / ethanol / 4 h / 25 °C / 760 Torr
With
pyridine; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; boron trifluoride diethyl etherate; hydrogen; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; pyridinium chlorochromate;
dmap; palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1002/hlca.19900730428