Multi-step reaction with 11 steps
1.1: potassium dihydrogenphosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 1 h / 85 °C
2.1: manganese(IV) oxide / chloroform / 6 h / 45 °C
3.1: dichloromethane; water / 0 °C
4.1: AD-mix β; tert-butyl alcohol; methanesulfonamide / water / 6 h / 20 °C
5.1: pyridinium p-toluenesulfonate / dichloromethane / 16 h / 20 °C
6.1: methanol; sodium methylate / tetrahydrofuran / 0.5 h / 0 - 20 °C
7.1: potassium hydrogencarbonate / N,N-dimethyl-formamide / 6 h / 40 °C
8.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 0 - 20 °C
9.1: methanol; sodium tetrahydroborate / 4 h / 20 °C
10.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 3 h / 20 °C
11.1: n-butyllithium / tetrahydrofuran / 1.5 h / -78 °C
11.2: 4 h / -78 °C
With
methanol; manganese(IV) oxide; sodium tetrahydroborate; potassium dihydrogenphosphate; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; methanesulfonamide; AD-mix β; sodium methylate; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; tert-butyl alcohol;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; chloroform; water; N,N-dimethyl-formamide;