Multi-step reaction with 13 steps
1.1: methanol; sodium methylate / 12 h / 20 °C / Inert atmosphere
2.1: toluene-4-sulfonic acid / acetonitrile / 3 h / 20 °C
3.1: sodium hydride / 1,4-dioxane / 60 °C / Inert atmosphere
4.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 20 °C / Inert atmosphere
5.1: methanol; toluene-4-sulfonic acid / 1 h / 70 °C
5.2: 20 °C
6.1: dichloromethane / 0.42 h / -78 °C / Inert atmosphere
7.1: pyridine / dichloromethane / 0.83 h / -78 °C / Inert atmosphere
8.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 14 h / -78 - 20 °C / Inert atmosphere; Molecular sieve
9.1: hydrazinium monoacetate / methanol / 12 h / Inert atmosphere; Reflux
10.1: pyridine / 0 - 20 °C / Inert atmosphere
11.1: hydrogen; palladium(II) hydroxide; acetic acid / methanol / 48 h / 3375.34 Torr
12.1: 1H-tetrazole / dichloromethane; acetonitrile / 2 h / 0 °C
13.1: tert.-butylhydroperoxide / dichloromethane; acetonitrile / 1 h / -40 - 0 °C / Inert atmosphere
With
pyridine; 1H-tetrazole; methanol; tert.-butylhydroperoxide; dmap; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium methylate; palladium(II) hydroxide; hydrazinium monoacetate; sodium hydride; toluene-4-sulfonic acid; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;
In
1,4-dioxane; methanol; dichloromethane; acetonitrile;
DOI:10.1021/ol2021687