Multi-step reaction with 10 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 20 °C
2.1: copper(l) iodide / tetrahydrofuran; dimethyl sulfate / 3 h / -30 °C
3.1: sodium periodate / tetrahydrofuran; water / 6 h / 20 °C
4.1: N-chloro-succinimide; (2R,5S)-2-tert-butyl 3,5-dimethylimidazolidin-4-one trifluoroacetic acid salt / acetonitrile / 2.5 h / 0 °C
4.2: 0.5 h
5.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / 0 - 20 °C
5.2: 1 h / -50 - -45 °C
5.3: 2 h / -70 - 0 °C
6.1: 2,6-dimethylpyridine; N-Bromosuccinimide; silver perchlorate / water; acetone / 0 - 0 h / 0 °C
7.1: samarium diiodide / tetrahydrofuran / 0.83 h / -20 °C
8.1: dmap; 2,4,6-trichlorobenzoyl chloride; dihydropyrimidinone / toluene / 7 h / 0 - 20 °C / Inert atmosphere
9.1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenyl-arsane / N,N-dimethyl-formamide / 1.5 h
10.1: Grela's catalyst; 2,3,5,6-tetrafluoro-1,4-benzoquinone / dichloromethane / 3 h / 60 °C / Inert atmosphere
10.2: 2 h / 20 °C
With
2,6-dimethylpyridine; dmap; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium periodate; N-chloro-succinimide; N-Bromosuccinimide; copper(l) iodide; n-butyllithium; samarium diiodide; triphenyl-arsane; 2,3,5,6-tetrafluoro-1,4-benzoquinone; (2R,5S)-2-tert-butyl 3,5-dimethylimidazolidin-4-one trifluoroacetic acid salt; 2,4,6-trichlorobenzoyl chloride; Grela's catalyst; silver perchlorate; 3-chloro-benzenecarboperoxoic acid; dihydropyrimidinone;
In
tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; dimethyl sulfate; acetonitrile;
5.3: Brook rearrangement / 7.1: Evans-Tishchenko reduction / 9.1: Stille coupling;
DOI:10.1002/anie.201108692