Multi-step reaction with 11 steps
1.1: diethyl ether / 1 h / -78 °C / Inert atmosphere
2.1: 20 % Pd(OH)2/C; hydrogen / ethanol; ethyl acetate / 18 h / 25 °C
3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 18 h / 25 °C / Inert atmosphere
4.1: dichloromethane / 4 h / 25 °C / Inert atmosphere
5.1: diisobutylaluminium hydride / dichloromethane / 1.5 h / -78 - 25 °C / Inert atmosphere
6.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
7.1: tris-(dibenzylideneacetone)dipalladium(0); (Me3Sn)2; trifuran-2-yl-phosphane; lithium chloride / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere
7.2: 3 h / 40 °C / Inert atmosphere
8.1: Oxone; sodium tetraborate heptahydrate; 1,2:4,5-di(O-i-propylidene)-3-deoxy-3-oxo-β-D-psicopyranose; tetra(n-butyl)ammonium hydrogensulfate; edetate disodium; potassium carbonate / Dimethoxymethane; water; acetonitrile / 3 h / 0 °C
9.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 0 - 25 °C
10.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0 - 25 °C / Inert atmosphere
11.1: sodium hexamethyldisilazane / tetrahydrofuran; toluene / 0.33 h / 0 °C / Inert atmosphere
11.2: 0.33 h / 0 °C / Inert atmosphere
With
2,6-dimethylpyridine; Oxone; tris-(dibenzylideneacetone)dipalladium(0); 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trifuran-2-yl-phosphane; [bis(acetoxy)iodo]benzene; 1,2:4,5-di(O-i-propylidene)-3-deoxy-3-oxo-β-D-psicopyranose; sodium tetraborate heptahydrate; 20 % Pd(OH)2/C; (Me3Sn)2; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; sodium hexamethyldisilazane; edetate disodium; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride;
In
tetrahydrofuran; diethyl ether; Dimethoxymethane; ethanol; dichloromethane; water; ethyl acetate; toluene; acetonitrile;
1.1: Grignard reaction / 7.2: Stille coupling / 8.1: Shi epoxidation / 11.1: Whiting reaction / 11.2: Whiting reaction;
DOI:10.1021/ja109531d