Multi-step reaction with 10 steps
1.1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,2-bis-(diphenylphosphino)ethane / 1,2-dichloro-ethane; toluene / 14 h / 25 °C / Inert atmosphere
2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium hydroxide / tetrahydrofuran; water / 25 h / 50 °C / Inert atmosphere; Sealed tube
3.1: periodic acid / ethyl acetate / 0.67 h / 25 °C
4.1: dimethylaluminum chloride / hexane; dichloromethane / 0.17 h / -78 °C / Inert atmosphere
4.2: 5 h / -78 °C / Inert atmosphere
5.1: dmap; triethylamine / dichloromethane; toluene / 1 h / 0 °C
6.1: 1.3-propanedithiol; triethylamine / methanol / 22 h / 25 °C
7.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 24 h / 25 °C / Inert atmosphere
8.1: sulfur; sodium tetrahydroborate / tetrahydrofuran / 1 h / 50 °C / Inert atmosphere
9.1: bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran; toluene / 21 h / 25 °C / Molecular sieve; Inert atmosphere
10.1: dichloro(3-phenyl-1H-inden-1-ylidene)bis(tricyclohexylphosphine)ruthenium(II) / dichloromethane / 25 - 40 °C / Inert atmosphere; Darkness
With
1.3-propanedithiol; sulfur; dmap; sodium tetrahydroborate; bis(1,5-cyclooctadiene)diiridium(I) dichloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; dichloro(3-phenyl-1H-inden-1-ylidene)bis(tricyclohexylphosphine)ruthenium(II); bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; dimethylaluminum chloride; periodic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; 1,2-bis-(diphenylphosphino)ethane; sodium hydroxide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; toluene;
1.1: Suzuki-Miyaura coupling / 2.1: Suzuki coupling;
DOI:10.1021/ol200160p