Multi-step reaction with 12 steps
1: 77 percent / SnCl4 / CH2Cl2 / 1 h / -78 °C
2: 96 percent / PPTS / CH2Cl2 / 3 h / 20 °C
3: OsO4; NaIO4; H2O / 2,6-lutidine / dioxane / 3 h / 20 °C
4: 185 mg / diethyl ether / 2 h / -78 °C
5: 89 percent / 2,6-lutidine / CH2Cl2 / 3 h / -78 °C
6: OsO4; NaIO4; H2O / 2,6-lutidine / dioxane / 3 h / 20 °C
7: 0.738 g / Ti(S,S)(TADDOL) / diethyl ether / 1 h / -78 °C
8: OsO4; NaIO4; H2O / 2,6-lutidine / dioxane / 3 h / 20 °C
9: 0.752 g / SnCl4 / CH2Cl2 / 1 h / -78 °C
10: 97 percent / PPTS / CH2Cl2 / 3 h / 20 °C
11: 92 percent / TBAF / tetrahydrofuran / 16 h / 20 °C
12: 88 percent / SO3*pyr; Et3N / CH2Cl2; dimethylsulfoxide / 72 h / 0 °C
With
2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; pyridine-SO3 complex; Ti(S,S)(TADDOL); tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; tin(IV) chloride; triethylamine;
2,6-dimethylpyridine;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/ol060812l