Multi-step reaction with 9 steps
1: 1.) LiClO4 / 1.) THF, 0 deg C, 10 min, 2.) THF, CH3CN, RT, 3 h
2: imidazole / CH2Cl2 / 18 h / Ambient temperature
3: Et3N / CH2Cl2 / 21 h / Ambient temperature
4: 1.) diisopropylamine, sec-butyllithium / 1.) THF, -70 deg C, 1.5 h, 2.) THF, RT, 16 h
5: Jone's reagent / acetone
6: DEPC, diisopropylethylamine / CH2Cl2 / 2 h / Ambient temperature
7: 1.) diisopropylamine, sec-butyllithium / 1.) THF, cyclohexane, -78 deg C, 35 min, 2.) THF, cyclohexane, from -78 deg C to RT, 1 h
8: 99 percent / NaBH4 / ethanol / Ambient temperature
9: 89 percent / N-methylmorpholine N-oxide, t-BuOH, OsO4 / acetone; H2O
With
1H-imidazole; sodium tetrahydroborate; osmium(VIII) oxide; Jones reagent; sec.-butyllithium; lithium perchlorate; 4-methylmorpholine N-oxide; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; diethyl dicarbonate; tert-butyl alcohol;
In
ethanol; dichloromethane; water; acetone;
DOI:10.1021/jm960092w