Multi-step reaction with 13 steps
1.1: 1H-imidazole; dmap / dichloromethane / 16 h / 20 °C / Inert atmosphere
2.1: sodium carbonate; ozone / dichloromethane / -78 °C / Inert atmosphere
2.2: 3 h / -78 - 20 °C / Inert atmosphere
3.1: sodium hexamethyldisilazane / toluene; 1,2-dimethoxyethane / 0.08 h / -78 °C / Inert atmosphere
3.2: 1 h / -50 °C / Inert atmosphere
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere
5.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 20 °C / Inert atmosphere
5.2: 2 h / 0 - 20 °C / Inert atmosphere
6.1: AD-mix β; methanesulfonamide / tert-butyl alcohol; water / 16 h / 0 - 20 °C
7.1: potassium carbonate / methanol / 4 h / 0 °C
8.1: 2,6-dimethylpyridine / dichloromethane / 1.5 h / -78 °C / Inert atmosphere
9.1: 10-camphorsufonic acid / dichloromethane; methanol / 1.5 h / 0 °C / Inert atmosphere
10.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere
11.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 - -50 °C / Inert atmosphere
11.2: 1.5 h / -78 °C / Inert atmosphere
12.1: toluene-4-sulfonic acid hydrazide; sodium acetate / 1,2-dimethoxyethane; water / 4 h / Reflux
13.1: dicyclohexyl-carbodiimide / dichloromethane / 0.25 h / 20 °C / Inert atmosphere
13.2: 16 h / 20 °C / Inert atmosphere
With
1H-imidazole; 2,6-dimethylpyridine; dmap; n-butyllithium; methanesulfonamide; AD-mix β; 10-camphorsufonic acid; tetrabutyl ammonium fluoride; sodium acetate; sodium hexamethyldisilazane; sodium hydride; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; Dess-Martin periodane; ozone; toluene-4-sulfonic acid hydrazide; dicyclohexyl-carbodiimide;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; dichloromethane; water; toluene; mineral oil; tert-butyl alcohol;
DOI:10.1002/chem.201204527