Multi-step reaction with 11 steps
1.1: potassium hydroxide / ethanol; water / 0.17 h / 0 °C
1.2: 0 - 20 °C
2.1: benzo[1,3,2]dioxaborole / tetrahydrofuran / -78 - 20 °C / Inert atmosphere
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
4.1: bromine; triethylamine; triphenylphosphine / dichloromethane / 0 - 20 °C
5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 24 h / 110 °C / Inert atmosphere
6.1: AD-mix β; methanesulfonamide / tetrahydrofuran; water; tert-butyl alcohol / 120 h / 0 °C
7.1: hydrogenchloride / methanol; diethyl ether; water / 6.5 h / Reflux; Inert atmosphere
8.1: pyridinium p-toluenesulfonate / dichloromethane / 1 h / 20 °C / Inert atmosphere
9.1: dichloromethane / 1.17 h / 0 °C / Inert atmosphere; Molecular sieve
10.1: potassium carbonate / acetone / 48 h / 20 °C / Inert atmosphere
10.2: 1.25 h / 20 °C / Inert atmosphere
11.1: dmap; triethylamine / dichloromethane / 16 h / 20 °C / Inert atmosphere
With
hydrogenchloride; dmap; lithium aluminium tetrahydride; methanesulfonamide; AD-mix β; bromine; pyridinium p-toluenesulfonate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; potassium hydroxide; benzo[1,3,2]dioxaborole;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; toluene; tert-butyl alcohol;
6.1: Sharpless dihydroxylation;
DOI:10.1016/j.bmcl.2011.09.116