Multi-step reaction with 14 steps
1.1: hydrogen iodide / water; toluene / 0.5 h / 0 - 20 °C
1.2: 2 h / Reflux
2.1: 1H-imidazole; dmap / dichloromethane / 24 h / 20 °C
3.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 24 h / -78 - 20 °C
4.1: platinum(II) chloride / toluene / 1.45 h / 80 °C
5.1: dimethylsulfide borane complex / tetrahydrofuran / 0 - 20 °C
5.2: 1 h / 0 - 20 °C
6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 20 °C
6.2: 3 h / 20 °C
7.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / Reflux
8.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 °C
9.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 °C
10.1: zinc dibromide / dichloromethane / 2 h / Inert atmosphere; Reflux
11.1: triethylamine / dichloromethane / 10 h
12.1: tetrabutyl ammonium fluoride / tetrahydrofuran
13.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / -78 °C / Reflux
14.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 1 h / -78 °C
With
1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen iodide; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; platinum(II) chloride; zinc dibromide;
In
tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; mineral oil;
3.1: Sonogashira coupling / 5.1: Hydroboration reaction / 7.1: Barton-McCombie deoxygenation / 9.1: Wittig reaction / 14.1: Swern oxidation;
DOI:10.1002/chem.201102101