Multi-step reaction with 11 steps
1: 97 percent / xylene / 14 h / Heating
2: NaBH4 / tetrahydrofuran; propan-2-ol / 16 h / Ambient temperature
3: 67 percent / PhPOCl2 / 3 h / 170 °C
4: 85 percent / dimethylformamide / 14 h / Heating
5: 2.) H2O, H(1+) / 1) C6H6, room temperature, 1.5 h
6: 96 percent / t-BuOK / toluene; 2-methyl-propan-2-ol / 10 h / Heating
7: 85 percent / TFA / 1 h / 0 °C
8: HNO3 / nitromethane / 0.42 h / 5 - 20 °C
9: K2CO3 / acetone / 5 h / Heating
10: OsO4, N-methylmorpholine N-oxide, H2O / acetone; 2-methyl-propan-2-ol / 20 h / Ambient temperature
11: NaIO4 / dioxane; H2O / 18 h / 80 °C
With
P,P-dichlorophenylphosphine oxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; potassium tert-butylate; water; nitric acid; hydrogen cation; potassium carbonate; 4-methylmorpholine N-oxide; trifluoroacetic acid;
In
tetrahydrofuran; 1,4-dioxane; nitromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetone; toluene; xylene; tert-butyl alcohol;
DOI:10.1021/ja00395a071