Multi-step reaction with 9 steps
1: 37 percent / p-toluenesulfonic acid, pyridinium p-toluenesulfonate / CH2Cl2 / 70 h / Heating
3: 90 percent / 2,6-lutidine / CH2Cl2 / 0.67 h
4: 1.) O3, 2.) NaBH4 / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2, methanol, RT, 7 h
5: 1.) triethylamine, methanesulfonyl chloride, 2.) NaBH4 / 1.) THF, 0 deg C, 1 h, 2.) CH2Cl2, ethanol, 80 deg C, 3 h
6: 30percent H2O2 / tetrahydrofuran / 0.5 h / Heating
7: 1.) n-butyllithium, TMEDA / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, -78 deg C, 20 min
8: 99.9 percent / tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / 1 h / Ambient temperature
9: 4-dimethylaminopyridine / CH2Cl2 / 0.67 h / 0 °C
With
2,6-dimethylpyridine; dmap; sodium tetrahydroborate; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; dihydrogen peroxide; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; ozone; methanesulfonyl chloride; triethylamine;
In
tetrahydrofuran; dichloromethane;