Multi-step reaction with 11 steps
1: 90 percent / NaBH4, CuCl*2H2O / methanol / 0 °C
2: 92 percent / LiAlH4 / tetrahydrofuran / 0 °C
3: 98 percent / imidazole / CH2Cl2 / 0 °C
4: 21 percent / I2, nBuLi / tetrahydrofuran
5: 92 percent / KOH / 1,2-dimethoxy-ethane
6: 84 percent / KH, Bu4NI / 1,2-dimethoxy-ethane / 0 °C
7: 68 percent / H2SO4
8: 64 percent / NaH / dimethylformamide
9: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 2) CH2Cl2, -78 to 0 deg C
10: 62 percent / TMSOTf / CH2Cl2 / -78 °C
11: 66 percent / TMSOTf / CH2Cl2 / -45 °C
With
1H-imidazole; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; iodine; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(98)00971-X