Multi-step reaction with 10 steps
1: 100 percent / 4-(dimethylamino)pyridine / pyridine / 72 h / 25 °C
2: 83 percent / 1percent aq. OsO4, potassium periodate / tetrahydrofuran; H2O / 31 h / 25 °C
3: 93 percent / 90percent H2O2, trifluoracetic anhydride, KH2PO4 / CH2Cl2 / 23 h / 0 °C
4: 58 percent / cation-exchange resin AG 50W-X4 / ethanol / 21 h / 25 °C
5: 96 percent / imidazole / dimethylformamide / 18 h / Ambient temperature
6: 100 percent / Zn, 1M KH2PO4 / tetrahydrofuran / 4.5 h / 25 °C
7: 99 percent / bis<α,α-bis(trifluoromethyl)benzenemethanolato>diphenylsulfur / CCl4 / 1.5 h / 25 °C
8: 87 percent / 1.09M NaOEt / ethanol / 0.5 h / 25 °C
9: 60 percent / (diethylamido)sulfur trifluoride / CH2Cl2 / 0.5 h / -95 °C
10: 85 percent / fluorenone / various solvent(s) / 1 h / Irradiation
With
1H-imidazole; dmap; potassium dihydrogenphosphate; osmium(VIII) oxide; potassium metaperiodate; Martins sulfurane; 9-fluorenone; (diethylamido)sulfur trifluoride; cation-exchange resin AG 50W-X4; dihydrogen peroxide; sodium ethanolate; trifluoroacetic anhydride; zinc;
In
tetrahydrofuran; pyridine; tetrachloromethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo00288a040