Multi-step reaction with 8 steps
1: 100 percent / K2CO3, KI / acetonitrile / 12 h / Heating
2: Ac2O, HNO3 / 1.) 0 deg C, 2 h, 2.) 25 deg C, 2 h
3: NaBH4 / ethanol / 4 h / 0 °C
4: tetrahydrofuran; toluene / 1.5 h / 25 °C
5: 1.) NaH / 1.) THF, 25 deg C, 30 min, 2.) THF, 0 deg C, 17 h
6: HNEt2 / Pd(PPh3)4 / tetrahydrofuran / 2.5 h / 25 °C
7: NEt3, DMAP / toluene; tetrahydrofuran / 25 °C
8: 75 percent / TBAF / tetrahydrofuran / 0.3 h
With
dmap; sodium tetrahydroborate; tetrabutyl ammonium fluoride; nitric acid; acetic anhydride; sodium hydride; potassium carbonate; diethylamine; triethylamine; potassium iodide;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; ethanol; toluene; acetonitrile;
DOI:10.1002/(SICI)1521-3765(19990301)5:3<951::AID-CHEM951>3.0.CO;2-G