Multi-step reaction with 5 steps
1: 1.) lithium diisopropylamide / 1.) THF, -82 deg C to -69 deg C, 45 min, 2.) THF, -69 deg C to -59 deg C, 1 h
2: 89 percent / MnO2 / CH2Cl2 / 2 h / Heating
3: 78 percent / MgCl2 / hexamethylphosphoric acid triamide / 2 h / 140 - 150 °C
4: 1.) n-BuLi / 1.) THF, hexane, a) -80 deg C to -75 deg C, 20 min, b) -20 deg C 10 min, 2.) THF hexane, -78 deg C, 20 min
5: 71 percent / NaIO4, OsO4 / tetrahydrofuran; H2O / 14 h / Ambient temperature
With
manganese(IV) oxide; sodium periodate; osmium(VIII) oxide; n-butyllithium; magnesium chloride; lithium diisopropyl amide;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water;
DOI:10.1248/cpb.42.846