Multi-step reaction with 11 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran; hexane / 1.25 h / -78 °C / Inert atmosphere
1.2: 5 h / -78 - -40 °C / Inert atmosphere
2.1: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 16.5 h / 0 - 20 °C
3.1: tetra(n-butyl)ammonium hydrogensulfate; Shi's ketone; Oxone; potassium carbonate; edetate disodium / acetonitrile / 9 h / 0 °C
4.1: triethylamine / dichloromethane / 3 h / 0 °C
5.1: sodium azide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 72 h / 60 °C
6.1: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; 1,4-dioxane / 6 h / 20 °C
7.1: triethylamine / tetrahydrofuran; water / 2 h / 0 °C
8.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 0.17 h / 0 °C
9.1: toluene / 1.5 h / 110 °C
10.1: caesium carbonate; thiophenol / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere
11.1: triethylamine / dichloromethane / 15 h / 20 °C
With
hydrogenchloride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; Oxone; sodium azide; Shi's ketone; lithium hydroxide monohydrate; palladium 10% on activated carbon; hydrogen; dihydrogen peroxide; tetra(n-butyl)ammonium hydrogensulfate; sodium hexamethyldisilazane; edetate disodium; potassium carbonate; caesium carbonate; thiophenol; triethylamine; triphenylphosphine; diethylazodicarboxylate;
In
tetrahydrofuran; 1,4-dioxane; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
3.1: |Shi Asymmetric Epoxidation / 8.1: |Mitsunobu Displacement;
DOI:10.1016/j.bmc.2013.03.022