Multi-step reaction with 10 steps
1.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 1.17 h / -78 - 20 °C / Inert atmosphere
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
2.2: 2 h / Inert atmosphere
3.1: palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / Inert atmosphere; Reflux
3.2: 1 h / -78 °C / Inert atmosphere
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.83 h / 0 °C / Inert atmosphere
5.1: triethylamine / dichloromethane / 24 h / 20 °C / Inert atmosphere; Reflux
6.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 0.5 h / 0 - 20 °C / Inert atmosphere
6.2: 1 h / Inert atmosphere; Reflux
7.1: dihydrogen peroxide / water / 1 h / 0 - 20 °C / Inert atmosphere
8.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
8.2: 3 h / -60 °C / Inert atmosphere
9.1: sodium amalgam; disodium hydrogenphosphate / tetrahydrofuran; methanol / 20 °C / Inert atmosphere
10.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0.5 h / 20 °C / Inert atmosphere
With
sodium tetrahydroborate; disodium hydrogenphosphate; sodium amalgam; lithium aluminium tetrahydride; ammonium cerium (IV) nitrate; oxalyl dichloride; dihydrogen peroxide; palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile;
1.1: Swern oxidation / 2.1: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.tetlet.2011.05.091