Multi-step reaction with 10 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C
2.1: sodium tetrahydroborate / ethanol / 2 h / 7 °C
3.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C
4.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -75 - -25 °C
4.2: 4 h / -60 - 0 °C
5.1: sodium periodate; osmium(VIII) oxide; water / tetrahydrofuran; tert-butyl alcohol / 4 h / 20 °C
6.1: acetic acid / tetrahydrofuran / 0.33 h / 20 °C
6.2: 12 h / 20 °C
7.1: boron tribromide / 1,1-dichloroethane; dichloromethane / 13 h / -20 - 20 °C
8.1: pyridine / dichloromethane / 1 h / 0 °C
9.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 3 h / 60 - 80 °C
10.1: sodium hydroxide; water / tetrahydrofuran / 12 h / 60 °C
With
pyridine; sodium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; water; boron tribromide; phosphorus tribromide; sodium carbonate; potassium carbonate; acetic acid; lithium diisopropyl amide;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; 1,1-dichloroethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;