Multi-step reaction with 14 steps
1: 18.4 g / toluene / 1 h / Heating
2: 80 percent / H2SO4 / 2-methyl-propan-2-ol / 22.5 h / Heating
3: Zn; iodine / tetrahydrofuran / 1.5 h / 20 - 50 °C
4: 5.23 g / p-toluenesulfonic acid monohydrate / toluene / 2 h / 20 °C
5: BBr3 / CH2Cl2 / 2 h / 0 °C
6: LiAlH4 / tetrahydrofuran / 2 h / 0 - 20 °C
7: 450 mg / K2CO3 / dimethylformamide / 17 h / 20 °C
8: 94 percent / p-toluenesulfonic acid monohydrate / tetrahydrofuran / 1.5 h / 20 °C
9: OsO4; aq. NaIO4 / 2-methyl-propan-2-ol; dioxane / 1 h / 0 - 20 °C
10: 412 mg / NaBH4 / tetrahydrofuran; dioxane; H2O / 0.67 h / 20 °C
11: pyridine / tetrahydrofuran / 16 h / 20 °C
12: 283 mg / aq. HCl / methanol / 2 h / 20 °C
13: Et3N / CH2Cl2 / 3.5 h / 0 °C
14: t-BuOK / dimethylformamide / 1 h / 20 °C
With
pyridine; hydrogenchloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; sulfuric acid; potassium tert-butylate; iodine; boron tribromide; potassium carbonate; toluene-4-sulfonic acid; triethylamine; zinc;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
1: Claisen rearrangement / 3: Reformatski reaction;
DOI:10.1021/jm050194z