Multi-step reaction with 13 steps
1.1: zinc(II) iodide / acetonitrile / 0.67 h / 0 °C / Inert atmosphere
2.1: Dess-Martin periodane / 3 h / 0 °C / Inert atmosphere
3.1: phenylborondichloride; N-ethyl-N,N-diisopropylamine / dichloromethane; methanol / 3.5 h / -78 °C / Inert atmosphere
4.1: benzo[1,3,2]dioxaborole / tetrahydrofuran / 20 h / -78 - 0 °C / Inert atmosphere
5.1: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 °C / Inert atmosphere
6.1: water; ethanol / 1.33 h / Reflux
7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1 h / 20 °C / Inert atmosphere
8.1: palladium 10% on activated carbon; hydrogen / ethanol / 24 h / Inert atmosphere
9.1: N-ethyl-N,N-diisopropylamine / toluene / 0.5 h / Inert atmosphere
10.1: dichloromethane / 1.5 h / 20 °C / Inert atmosphere
11.1: N-ethyl-N,N-diisopropylamine / toluene / 1.33 h / 40 °C
11.2: 6 h / 20 °C / Inert atmosphere
12.1: N-ethyl-N,N-diisopropylamine / toluene / 4 h / 0 °C / Inert atmosphere
13.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / Inert atmosphere
With
2,6-dimethylpyridine; palladium 10% on activated carbon; phenylborondichloride; hydrogen; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) iodide; benzo[1,3,2]dioxaborole;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; toluene; acetonitrile;
DOI:10.1021/ja3057612