Multi-step reaction with 12 steps
1: 92 percent / 30percent H2O2, 10percent aq. NaOH / methanol / 12 h / 0 °C
2: 82 percent / p-toluenesulfonohydrazide, silica gel / CH2Cl2 / 1.) -20 deg C, 12 h, 2.) r.t, 4 h
3: 1.) THF, ether, -78 deg C, 1.5 h, 2.) HMPA, -78 deg C, 2 h
4: 1.) Pyrex glass powder, 2.) CuI / 1.) 210 deg C, 100 mm Hg, 30 min, 2.) THF, ether, -78 deg C, 2 h
5: 97 percent / diisobutylaluminum hydride / diethyl ether; cyclohexane / 0.5 h / -78 °C
6: tert-butyl hydroperoxide, VO(acac)2 / benzene / 40 °C
7: 1.) OsO4, 2.) NaHSO4 / 1.) pyridine, r.t., overnight, 2.) water, pyridine, r.t., 2 h
8: camphorsulfonic acid / CH2Cl2 / 1.) 0 deg C, 15 min, 2.) to r.t.
9: 91 percent / anhydr. CuSO4 / 48 h / Heating
10: 96 percent / CrO3 / pyridine / 168 h / 30 °C
11: 87 percent / NaBH4 / ethanol / 1 h / Ambient temperature
12: 98 percent / camphorsulfonic acid / methanol / 3 h / Ambient temperature
With
chromium(VI) oxide; tert.-butylhydroperoxide; sodium hydroxide; sodium tetrahydroborate; sodium hydrogen sulfate; copper(l) iodide; osmium(VIII) oxide; bis(acetylacetonate)oxovanadium; camphor-10-sulfonic acid; dihydrogen peroxide; silica gel; diisobutylaluminium hydride; copper(II) sulfate; toluene-4-sulfonic acid hydrazide;
In
pyridine; methanol; diethyl ether; ethanol; dichloromethane; cyclohexane; benzene;
DOI:10.1021/jo00027a013