Multi-step reaction with 15 steps
1.1: sodium tetrahydroborate / ethanol / 0 °C / Inert atmosphere
2.1: 1H-imidazole / N,N-dimethyl-formamide / 20 h / -40 °C / Inert atmosphere
3.1: pyridinium p-toluenesulfonate / dichloromethane / 48 h / 0 °C / Inert atmosphere
4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere
4.2: 0.5 h / Inert atmosphere
5.1: pyridinium p-toluenesulfonate / ethanol / 12 h / 55 °C / Inert atmosphere
6.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere
7.1: tetrahydrofuran / 13 h / Inert atmosphere; Reflux
8.1: lithium borohydride / ethanol / 4 h / Inert atmosphere
9.1: palladium 10% on activated carbon; ammonium formate / methanol / 12.5 h / Inert atmosphere
10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / Inert atmosphere
11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / Inert atmosphere
12.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere
13.1: copper(II) sulfate / toluene / 12 h / 20 °C / Inert atmosphere
14.1: tetrahydrofuran; chlorobenzene / 1 h / Inert atmosphere; Reflux
15.1: palladium 10% on activated carbon; hydrogen / isopropyl alcohol / 24 h / Inert atmosphere
With
1H-imidazole; sodium tetrahydroborate; lithium borohydride; n-butyllithium; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; ammonium formate; pyridinium p-toluenesulfonate; Dess-Martin periodane; copper(II) sulfate; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; chlorobenzene; isopropyl alcohol; toluene;
14.1: |Grignard Reaction;
DOI:10.1021/ol400469w