Multi-step reaction with 8 steps
1: 95 percent / pyridinium tosylate / ethanol / 4 h / 55 °C
2: 99 percent / MnO2 / hexane
3: 95 percent / tetrahydrofuran / -78 - 23 °C
4: 95 percent / Bu4NF / tetrahydrofuran
5: 94 percent / (-)-diethyl tartrate, Ti(O-i-Pr)4, t-BUOOH, 4 Angstroem molecular sieves / CH2Cl2
6: 94 percent / n-Bu4NI / tetrahydrofuran
7: 86 percent / TiCl4 / CH2Cl2 / 0.17 h / -94 °C
8: 1.) Dess-Martin periodinane, 2.) H2NNH2, K2CO3, 3.) OsO4, 4.) NaIO4 / 1) CH2Cl2; 2) bis(ethylene glycol), 210 deg C; 3) t-BuOH-H2O; 4) dioxane, H2O
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; manganese(IV) oxide; sodium periodate; osmium(VIII) oxide; 4 A molecular sieve; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; potassium carbonate; Dess-Martin periodane; (-)-diethyl tartrate; hydrazine;
In
tetrahydrofuran; ethanol; hexane; dichloromethane;
DOI:10.1021/ja972549c