Multi-step reaction with 15 steps
1: 84 percent / p-toluenesulfonic acid monohydrate / benzene / 7 h / Heating
2: N-methylmorpholine N-oxide monohydrate, osmium tetraoxide / acetone; H2O; 2-methyl-propan-2-ol / 2 h / 23 °C
3: 95 percent / sodium periodate / dioxane; H2O / 1 h / 23 °C
4: 1.) n-butyllithium / 1.) THF/hexane, -78 deg C, 10 min, 2.) -78 deg C, 1 h
5: 94 percent / pyridine, chromium trioxide, molecular sieves 4A / CH2Cl2 / 0.5 h / 23 °C
6: H2 / 10percent Pd/C / ethanol / 60 h / 23 °C
7: 1.) potassium tert-butoxide (tBuOK) / 1.) THF, 23 deg C, 15 min, 2.) THF, 23 deg C, 1 h
8: 96 percent / D-(-)-diethyl tartrate ((-)-DET), molecular sieves 4A, titanium(IV) isopropoxide, tert-butyl hydroperoxide (TBHP) / CH2Cl2 / 5 h / -20 °C
9: 1.) potassium hydride / 1.) THF, 23 deg C, 20 min, 2.) 23 deg C, 32 h
10: 93 percent / triethylamine, sulfur trioxide pyridine complex / dimethylsulfoxide / 1 h / 23 °C
11: 1.) potassium tert-butoxide (tBuOK) / 1.) THF, 23 deg C, 20 min, 2.) 50 deg C, 48 h
12: 100 percent / iron(III) chloride / acetone / 5 h / 23 °C
13: 1.) LDA, 2.) oxodiperoxymolybdenum(pyridine)(hexamethylphosphoric triamide) (MoOPH) / 1.) THF/hexane, -78 deg C, 30 min, 2.) -30 deg C, 10 min
14: 99 percent / triethylamine / CH2Cl2 / 1 h / 0 °C
15: 75 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C
With
pyridine; 2,6-dimethylpyridine; chromium(VI) oxide; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; osmium(VIII) oxide; n-butyllithium; MoO5*pyridine*HMPA; diethyl (2S,3S)-tartrate; 4 A molecular sieve; potassium tert-butylate; hydrogen; sulfur trioxide pyridine complex; iron(III) chloride; potassium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; lithium diisopropyl amide;
palladium on activated charcoal;
In
1,4-dioxane; ethanol; dichloromethane; water; dimethyl sulfoxide; acetone; tert-butyl alcohol; benzene;
DOI:10.1021/jo00275a020
