Multi-step reaction with 12 steps
1: 29.8 g / KMnO4 / H2O / 12 h / 90 °C
2: thionyl chloride / 4 h / Heating
3: 25.0 g / 1 h / Heating
4: 77 percent / NaBH4 / ethanol / 16 h / Heating
5: 98 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 - 20 °C
6: 36 percent / n-BuLi / hexane; tetrahydrofuran / 2.5 h / -78 - 20 °C
7: 60 percent / pyridine; triethylamine; methanesulfonyl chloride / 4 h / 0 - 20 °C
8: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 20 °C
9: 1.58 g / TEMPO; sodium chlorite; sodium hypochlorite / acetonitrile; aq. phosphate buffer / 35 °C
10: 59 percent / hexane; ethanol / 0.5 h / 20 °C
11: 98 percent / TFA / CH2Cl2 / 0.5 h / 20 °C
12: 53 percent / pyridine; triethylamine / 20 °C
With
pyridine; 2,6-dimethylpyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; sodium tetrahydroborate; potassium permanganate; n-butyllithium; thionyl chloride; tetrabutyl ammonium fluoride; methanesulfonyl chloride; triethylamine; trifluoroacetic acid;
In
tetrahydrofuran; phosphate buffer; ethanol; hexane; dichloromethane; water; acetonitrile;
DOI:10.1016/j.bioorg.2003.09.001