Multi-step reaction with 17 steps
1.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C / Inert atmosphere
2.1: potassium osmate monohydrate; 4-methylmorpholine N-oxide / water; acetone / 4 h / 20 °C
3.1: 2,6-dimethylpyridine / dichloromethane / 0.42 h / -30 °C / Inert atmosphere
4.1: dmap; magnesium bromide diethyl etherate; N-ethyl-N,N-diisopropylamine / dichloromethane / 144 h / 20 °C / Inert atmosphere
5.1: potassium osmate monohydrate; 4-methylmorpholine N-oxide / water; acetone / 1 h / 20 °C
6.1: pyridinium p-toluenesulfonate / methanol / 3.5 h / 0 °C / Inert atmosphere
7.1: triethylamine / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere
8.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 1.5 h / 110 °C
9.1: triethylamine; hydrazine / tetrahydrofuran; ethanol / 4.5 h / 80 °C
10.1: iodine; triethylamine / tetrahydrofuran; ethanol / 2 h / 20 °C / Inert atmosphere
11.1: tetrakis(triphenylphosphine) palladium(0); tri-n-butyl-tin hydride / benzene / 1.5 h / 20 °C / Inert atmosphere
12.1: pyridinium p-toluenesulfonate / ethanol / 120 h / 20 °C / Inert atmosphere
13.1: sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; potassium bromide / dichloromethane; water / 2.5 h / 0 - 20 °C
13.2: 1.5 h / 20 °C
14.1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 20 °C
15.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.08 h / -78 °C / Inert atmosphere
16.1: tetrakis(triphenylphosphine) palladium(0); phenylsilane / dichloromethane / 4 h / 20 °C / Inert atmosphere
17.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3.5 h / 20 °C / Inert atmosphere
With
2,6-dimethylpyridine; dmap; sodium hypochlorite; tetrakis(triphenylphosphine) palladium(0); 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; magnesium bromide diethyl etherate; 2,2'-azobis(isobutyronitrile); potassium osmate monohydrate; phenylsilane; iodine; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydrogencarbonate; potassium carbonate; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; potassium bromide; hydrazine;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; benzene;
6.1: Barton-McCombie deoxygenation / 11.1: Stille coupling;
DOI:10.1021/ol301090v