Multi-step reaction with 12 steps
1.1: dmap; triethylamine / dichloromethane / 0.5 h / 20 °C
1.2: 2 h / 20 °C
2.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / water; acetonitrile / 15 h / 0 °C
3.1: methanol / diethyl ether / 0 °C
4.1: toluene-4-sulfonic acid / toluene / 12 h / Reflux
5.1: lithium diisopropyl amide / tetrahydrofuran / -78 °C
5.2: 0.25 h
6.1: sodium tetrahydroborate / methanol / 2 h / -40 °C
7.1: pyridinium p-toluenesulfonate / dichloromethane / 3 h / Reflux
8.1: diisobutylaluminium hydride / tetrahydrofuran / 9 h / -5 °C
9.1: dmap; triethylamine / dichloromethane / 3 h / Reflux
10.1: dimethylaluminum chloride / hexane; dichloromethane / 0.5 h / 0 - 20 °C
11.1: 1-methyl-2-azaadamantane-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 12 h / 20 °C
12.1: Wilkinson's catalyst; diethylzinc / tetrahydrofuran / 3 h / -20 °C
With
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; diethylzinc; dimethylaluminum chloride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene; acetonitrile;
5.1: Claisen condensation / 5.2: Claisen condensation / 12.1: Reformatsky reaction;
DOI:10.3987/COM-10-12042