Multi-step reaction with 15 steps
1.1: ozone / dichloromethane; methanol / -78 °C
1.2: -78 - 0 °C
2.1: 1H-imidazole / tetrahydrofuran; dichloromethane / 0 - 20 °C
3.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 20 °C / Molecular sieve
4.1: n-butyllithium / tetrahydrofuran / 0 - 20 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C
6.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C
7.1: camphor-10-sulfonic acid / dichloromethane; methanol / 20 °C
8.1: 1H-imidazole / N,N-dimethyl-formamide / 61.5 h / 50 °C
9.1: pyridinium p-toluenesulfonate / dichloromethane; methanol / 0.17 h / -10 °C
10.1: triethylamine; sulfur trioxide pyridine complex; dimethyl sulfoxide / dichloromethane / 0.5 h / 0 °C
11.1: sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogenphosphate / water; tert-butyl alcohol / 2 h / 0 - 20 °C
12.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 16 h / 0 - 20 °C
13.1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; ((diphenylphosphoryl)oxy)copper(I); triphenyl-arsane / tetrahydrofuran / 3 h / 20 °C
14.1: zinc(II) tetrahydroborate / diethyl ether / 7.5 h / -40 °C
15.1: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 - 20 °C
With
1H-imidazole; 2,6-dimethylpyridine; dmap; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; tetrapropylammonium perruthennate; zinc(II) tetrahydroborate; 2-methyl-but-2-ene; ((diphenylphosphoryl)oxy)copper(I); triphenyl-arsane; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; sodium hydride; ozone; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; dicyclohexyl-carbodiimide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
10.1: |Parikh-Doering Oxidation;
DOI:10.1246/bcsj.20120152