Multi-step reaction with 13 steps
1: 90.3 percent / NaBH4 / ethanol
2: hydrogen / PtO2 / methanol
3: 2,6-lutidune / CH2Cl2
4: 85 percent / p-TsOH / methanol
5: LiBr / acetone
6: 1.) Mg 2.) 3P>4 / THF
7: n-BuF4 / tetrahydrofuran
8: Na2Cr2O7*2H2O, H2SO4 / acetic acid / Ambient temperature
9: 78 percent / LiH / tetrahydrofuran; hexamethylphosphoric acid triamide / 48 h / Heating
10: 73 percent / DIBAL-H / hexane / 24 h / -78 °C
11: 94 percent / MnO2 / CH2Cl2 / 3 h / Ambient temperature
12: 1.) n-BuLi / 1.) THF, -78 deg C 2.) room temperature, 10 h
13: 94 percent / DIBAL-H / hexane / 1 h / -78 °C
With
2,6-dimethylpyridine; manganese(IV) oxide; sodium tetrahydroborate; n-butyllithium; sodium dichromate; tetrakiscopper(I); sulfuric acid; hydrogen; lithium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; magnesium; lithium bromide;
platinum(IV) oxide;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; hexane; dichloromethane; acetic acid; acetone;
DOI:10.1016/S0040-4039(00)95054-8