Multi-step reaction with 11 steps
1.1: sodium tetrahydroborate / methanol / 1.25 h / -78 °C / Inert atmosphere
2.1: pyridine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere
3.1: potassium dihydrogenphosphate / tert-butyl methyl ether; pentane / 20 °C / pH 7 / Resolution of racemate; Enzymatic reaction
4.1: lithium hydroxide monohydrate / methanol; water / 0.5 h / 20 °C
5.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
6.1: ozone / dichloromethane; methanol / -78 °C
6.2: dehumidified air / 3 h / -78 - 20 °C
7.1: dmap; pyridine / dichloromethane / 2 h / -42 °C / Inert atmosphere
8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / Inert atmosphere; Reflux
9.1: potassium carbonate / dichloromethane; methanol / 1 h / Inert atmosphere
10.1: zinc / tetrahydrofuran / 0.5 h / 40 °C / Inert atmosphere; Reflux
11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / Inert atmosphere; Reflux
With
pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; potassium dihydrogenphosphate; lithium hydroxide monohydrate; potassium carbonate; ozone; zinc; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; dichloromethane; tert-butyl methyl ether; water; ethyl acetate; N,N-dimethyl-formamide; pentane;
10.1: |Barbier Coupling Reaction;
DOI:10.1002/anie.201400617