Multi-step reaction with 12 steps
1: SmI2 / tetrahydrofuran; hexamethylphosphoric acid triamide / Ambient temperature
2: 93 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C
3: 100 percent / NaH / dimethylformamide / 2 h / Ambient temperature
4: 1.) O3, 2.) PPh3 / 1.) MeOH, -78 deg C, 10 min, 2.) -78 deg C to r.t.
5: 87 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C
6: 99 percent / Et3N / CH2Cl2 / 2 h / 0 °C
7: 86 percent / dimethylsulfoxide / 6 h / 60 °C
8: 99 percent / Et3N / CH2Cl2 / 1 h / 0 °C
9: 86 percent / KO-t-Bu / tetrahydrofuran / 2 h / Ambient temperature
10: 94 percent / DIBAL / tetrahydrofuran; hexane / 2 h / -78 °C
11: 96 percent / NaBH4 / tetrahydrofuran / 12 h / Ambient temperature
12: Et3N / CH2Cl2 / 0.5 h / 0 °C
With
sodium tetrahydroborate; lithium aluminium tetrahydride; samarium diiodide; potassium tert-butylate; sodium hydride; diisobutylaluminium hydride; ozone; triethylamine; triphenylphosphine;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1039/p19960002291