Multi-step reaction with 8 steps
1.1: tert.-butyl lithium; 9-methoxy-9-BBN / tetrahydrofuran; diethyl ether; hexane; pentane / 1 h / -78 - 20 °C / Inert atmosphere
1.2: 20 h / 20 °C / Inert atmosphere; Darkness
2.1: hydrogenchloride / ethanol / 0.33 h / 20 °C / Inert atmosphere
3.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere
4.1: 18-crown-6 ether; potassium carbonate / N,N,N,N,N,N-hexamethylphosphoric triamide; toluene / 18 h / -10 - -5 °C / Inert atmosphere
5.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1.5 h / 0 °C / pH 7 / aq. buffer
6.1: dichloromethane / 1.5 h / 20 °C / Inert atmosphere
6.2: 2 h / 20 °C / Inert atmosphere
7.1: potassium tri-sec-butyl-borohydride / tetrahydrofuran; toluene / 2 h / -78 °C / Inert atmosphere
7.2: -78 °C / Inert atmosphere
8.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / Inert atmosphere
With
hydrogenchloride; dmap; 18-crown-6 ether; water; tert.-butyl lithium; sulfur trioxide pyridine complex; potassium tri-sec-butyl-borohydride; potassium carbonate; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 9-methoxy-9-BBN; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; hexane; dichloromethane; toluene; pentane;
1.2: Suzuki coupling / 3.1: Parikh-Doering oxidation / 4.1: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.bmc.2011.06.082