Multi-step reaction with 11 steps
1: 1.) NaBH4, CeCl3*6H2O, 2.) LiAlH4, AlCl3 / 1.) MeOH, 0 deg C, 15 min, 2.) Et2O, 0 deg C, 5 h
2: Pri2NEt / CH2Cl2 / 8 h / Heating
3: 1.) BH3, 2.) NaOH, 30percent H2O2 / 1.) THF, 0 deg C, 2 h, 2.) 20 deg C, 1 h
4: PCC / CH2Cl2 / 2 h / 20 °C
5: NaH / benzene / 3 h / 60 °C
7: oxalic acid / methanol; H2O / 1 h / 25 °C
8: Me4NOAc, HMPA / 16 h / 100 °C
9: CuBr / tetrahydrofuran / 1 h / -40 °C
10: NaBH4, / methanol / 0.17 h / 0 °C
11: py / 16 h / 25 °C
With
pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; aluminium trichloride; cerium(III) chloride; borane; tetramethyl ammonium acetate; dihydrogen peroxide; oxalic acid; sodium hydride; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; copper(I) bromide;
In
tetrahydrofuran; methanol; dichloromethane; water; benzene;
DOI:10.1016/S0040-4039(00)98597-6