Multi-step reaction with 11 steps
1.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 0 °C
2.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C
2.2: 2.5 h / 20 °C
3.1: Oxone; C13H20O9; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / Dimethoxymethane; water; acetonitrile / 24 h / 0 °C / pH 6 / aq. phosphate buffer
4.1: water; pyridinium p-toluenesulfonate / 1,4-dioxane / 12 h / 70 °C
5.1: [bis(acetoxy)iodo]benzene; potassium hydroxide / 2 h / 0 °C
6.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
7.1: pyridine; pyridine hydrofluoride / tetrahydrofuran / 8 h / -78 - 0 °C
8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0 - 20 °C
9.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere
9.2: -78 °C / Inert atmosphere
10.1: toluene-4-sulfonic acid / tetrahydrofuran; water / 4.5 h / Reflux
11.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C
With
pyridine; 2,6-dimethylpyridine; Oxone; sodium tetrahydroborate; n-butyllithium; C13H20O9; pyridine hydrofluoride; [bis(acetoxy)iodo]benzene; water; tetra(n-butyl)ammonium hydrogensulfate; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; potassium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; Dimethoxymethane; hexane; dichloromethane; water; acetonitrile; mineral oil;
3.1: Shi epoxidation / 8.1: Dess-Martin oxidation / 11.1: Dess-Martin oxidation;
DOI:10.1002/anie.201006528