Multi-step reaction with 10 steps
1.1: hydrogenchloride / ethanol; water / Inert atmosphere
2.1: triethylamine; magnesium chloride / acetonitrile / 0.5 h / Inert atmosphere; Reflux
3.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 0 °C / Inert atmosphere
4.1: potassium tert-butylate / tetrahydrofuran / 2.08 h / -78 - 0 °C / Inert atmosphere
4.2: 16.08 h / 20 °C / Inert atmosphere
5.1: AD-mix-β; water / tert-butyl alcohol / 3 h / 20 °C / Inert atmosphere
6.1: dmap; triethylamine / dichloromethane / 18 h / 20 °C / Inert atmosphere
7.1: sodium hydride / tetrahydrofuran / 0.67 h / 0 - 20 °C / Inert atmosphere; Cooling with ice
7.2: 3 h / 20 °C / Inert atmosphere
8.1: triethylsilane; trifluoroacetic acid / dichloromethane / 0.17 h / 20 °C / Inert atmosphere
9.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.27 h / -78 °C / Inert atmosphere
9.2: 3.02 h / Inert atmosphere; Cooling with ice
10.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere
10.2: 3 h / Inert atmosphere; Cooling with ice
With
hydrogenchloride; triethylsilane; dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; AD-mix-β; potassium tert-butylate; water; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; magnesium chloride;
In
tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
2.1: Casiraghi/Hoflokken ortho-formylation / 5.1: Sharpless dihydroxylation / 9.1: Swern oxidation / 9.2: Swern oxidation / 10.1: Lindgren-Kraus oxidation;
DOI:10.1016/j.tet.2011.04.094