Multi-step reaction with 11 steps
1.1: n-butyllithium / tetrahydrofuran; hexanes / 1 h / -78 °C / Inert atmosphere
1.2: 1 h / -78 °C / Inert atmosphere
2.1: hydrazine hydrate / ethanol / 12 h / Reflux; Inert atmosphere
3.1: 1 h / 75 °C / Inert atmosphere
4.1: lead(IV) tetraacetate / tetrahydrofuran / 1 h / 25 °C / Inert atmosphere
5.1: ammonium acetate; ammonium chloride / ethanol; acetic acid / 0.5 h / 90 °C / Inert atmosphere
6.1: boron trifluoride diethyl etherate; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere
7.1: ethylmagnesium bromide / tetrahydrofuran / 2 h / 50 °C / Inert atmosphere
7.2: 16 h / 25 - 70 °C / Inert atmosphere
8.1: sulfuric acid; water / tetrahydrofuran / 1 h / 75 °C
8.2: 0.17 h / 25 °C
9.1: water; sodium hydroxide / tetrahydrofuran; methanol / 25 °C
10.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1 h / Inert atmosphere
11.1: 0.08 h / 25 °C / Inert atmosphere
With
dmap; n-butyllithium; sulfuric acid; boron trifluoride diethyl etherate; ethylmagnesium bromide; ammonium acetate; water; lead(IV) tetraacetate; ammonium chloride; hydrazine hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; sodium hydroxide;
In
tetrahydrofuran; methanol; hexanes; ethanol; dichloromethane; acetic acid;
DOI:10.1021/jo200246q