Multi-step reaction with 12 steps
1.1: 97 percent / NaOH; H2O / dioxane / 0.5 h / 0 °C
2.1: 75 percent / 1,3-dicyclohexylcarbodiimide; 1-hydroxybenzotriazole hydrate; N-methyl morpholine / dimethylformamide; CH2Cl2 / 24 h / 20 °C
3.1: bis(trifluoroacetoxy)iodobenzene; MeOH / CH2Cl2; methanol / 0.17 h / 0 °C
3.2: 69 percent / H2O / 0.08 h / 0 °C
4.1: 96 percent / H2 / Pd/C / ethyl acetate / 6 h / 20 °C / 760.05 Torr
5.1: 90 percent / pyridinium p-toluenesulfonate / benzene / 3.5 h / Heating
6.1: 65 percent / LiAlH4 / tetrahydrofuran / 11 h / Heating
7.1: 91 percent / Et3N / CH2Cl2 / 3 h / 0 - 20 °C
8.1: 84 percent / Zn; AcOH / 5 h / 75 °C
9.1: 86 percent / K2CO3 / acetonitrile / 15 h / 35 - 40 °C
10.1: H2 / Pd/C / methanol / 0.5 h / 20 °C / 760.05 Torr
11.1: 60 mg / diphenylphosphoryl azide; NaHCO3 / dimethylformamide; CH2Cl2 / 87 h / 0 - 20 °C
12.1: lithium diisopropylamide / tetrahydrofuran; pentane / 0.42 h / 0 °C
12.2: 80 percent / tetrahydrofuran; pentane / 1.5 h / -78 °C
With
4-methyl-morpholine; methanol; sodium hydroxide; lithium aluminium tetrahydride; diphenylphosphoranyl azide; water; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; acetic acid; 1-hydroxybenzotriazol-hydrate; triethylamine; dicyclohexyl-carbodiimide; bis-[(trifluoroacetoxy)iodo]benzene; zinc; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; pentane; benzene;
DOI:10.1021/ol015626o