Multi-step reaction with 19 steps
1.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / water; acetonitrile / 15 h / 0 °C
2.1: methanol / diethyl ether / 0 °C
3.1: toluene-4-sulfonic acid / toluene / 12 h / Reflux
4.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C
4.2: 0.25 h
5.1: sodium tetrahydroborate / methanol / 2 h / -40 °C
6.1: pyridinium p-toluenesulfonate / dichloromethane / 3 h / Reflux
7.1: diisobutylaluminium hydride / tetrahydrofuran / 9 h / -5 °C
8.1: dmap; triethylamine / dichloromethane / 3 h / Reflux
9.1: dimethylaluminum chloride / hexane; dichloromethane / 0.5 h / 0 - 20 °C
10.1: 1-methyl-2-azaadamantane-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 12 h / 20 °C
11.1: Wilkinson's catalyst; diethylzinc / tetrahydrofuran / 3 h / -20 °C
12.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 12 h / 0 °C
13.1: sodium cyanoborohydride; acetic acid / tetrahydrofuran / 144 h / 0 °C
14.1: hydrogenchloride / 2,2,2-trifluoroethanol; water / 0.5 h / 20 °C
15.1: dmap; triethylamine / dichloromethane / 12 h / 20 °C
16.1: methanol / 2.5 h / 20 °C
17.1: dmap; triethylamine / dichloromethane / 12 h / 20 °C
18.1: silica gel / chloroform; ethyl acetate / 0.25 h
19.1: 2-azaadamantane-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 4 h / 20 °C
With
hydrogenchloride; methanol; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium tetrahydroborate; Wilkinson's catalyst; 1-methyl-2-azaadamantane-N-oxyl; [bis(acetoxy)iodo]benzene; 2-azaadamantane-N-oxyl; diethylzinc; dimethylaluminum chloride; pyridinium p-toluenesulfonate; silica gel; diisobutylaluminium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; chloroform; 2,2,2-trifluoroethanol; water; ethyl acetate; toluene; acetonitrile;
4.1: Claisen condensation / 4.2: Claisen condensation / 11.1: Reformatsky reaction;
DOI:10.3987/COM-10-12042