Multi-step reaction with 12 steps
1.1: ozone / dichloromethane / 1 h / -78 °C
1.2: 16 h / 20 °C / Inert atmosphere
2.1: indium(III) chloride; water; (S)-[1,1']-binaphthalenyl-2,2'-diol / tetrahydrofuran; dichloromethane / 0.33 h / Inert atmosphere
2.2: 36 h / 20 °C
3.1: triethylamine / dichloromethane / 0 - 20 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 °C
5.1: sodium acetate; pyridinium chlorochromate / dichloromethane / 3 h / 0 °C
6.1: potassium tri-sec-butyl-borohydride / tetrahydrofuran / 3 h / -78 °C
7.1: 1H-imidazole / dichloromethane / 12 h / 25 °C
8.1: water; trifluoroacetic acid / 3 h / 9 °C
9.1: sodium periodate; water / acetonitrile / 20 °C
10.1: magnesium / tetrahydrofuran
10.2: 3 h / -30 °C
11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 °C
12.1: pyridinium p-toluenesulfonate / 1 h / 20 °C
With
1H-imidazole; indium(III) chloride; sodium periodate; tetrabutyl ammonium fluoride; water; (S)-[1,1']-binaphthalenyl-2,2'-diol; sodium acetate; pyridinium p-toluenesulfonate; potassium tri-sec-butyl-borohydride; ozone; magnesium; triethylamine; pyridinium chlorochromate; trifluoroacetic acid;
In
tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1055/s-0030-1260014