Multi-step reaction with 17 steps
1.1: toluene-4-sulfonic acid / acetone / 6 h / 0 °C
2.1: triethylamine / tetrahydrofuran / 1 h / -30 °C / Inert atmosphere
3.1: lithium bromide / tetrahydrofuran / 0.5 h / 0 °C
4.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
4.2: 20 °C
5.1: sodium hydroxide / tetrahydrofuran / 5 h / Reflux
5.2: 0 °C
6.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere
6.2: 20 °C
7.1: methanesulfonamide; AD-mix β / tert-butyl alcohol; water / 0 °C
8.1: toluene-4-sulfonic acid / dichloromethane / 20 °C
9.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -78 °C / Inert atmosphere
10.1: triethylamine / tetrahydrofuran / 1 h / Inert atmosphere
11.1: lithium bromide / tetrahydrofuran / 0.5 h / 0 °C
12.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
12.2: 20 °C
13.1: sodium hydroxide / tetrahydrofuran / 5 h / 0 °C / Reflux
14.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere
14.2: 20 °C
15.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -78 °C / Inert atmosphere
16.1: trifluoroacetic acid / methanol; water / 20 °C
17.1: 1H-imidazole / N,N-dimethyl-formamide / -30 °C
With
1H-imidazole; methanesulfonamide; AD-mix β; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; lithium bromide; sodium hydroxide;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;
DOI:10.1021/ja3116636