Multi-step reaction with 8 steps
1.1: tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
2.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere
2.2: 1.5 h / 0 - 20 °C / Inert atmosphere
3.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / tetrahydrofuran; tert-butyl alcohol / 20 °C
4.1: sodium periodate / tetrahydrofuran; water; tert-butyl alcohol / 1 h / 20 °C
5.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 0.83 h / 0 - 20 °C
5.2: 0 °C
6.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
7.1: copper(l) iodide; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; trifuran-2-yl-phosphane; triethylamine / N,N-dimethyl-formamide / 4.4 h / 50 °C / Inert atmosphere
8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 0 - 20 °C / pH 7 / buffer
With
dmap; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; copper(l) iodide; osmium(VIII) oxide; 2-methyl-but-2-ene; trifuran-2-yl-phosphane; potassium tert-butylate; water; 4-methylmorpholine N-oxide; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1016/j.tet.2011.03.114