Multi-step reaction with 15 steps
1: 6 h / 0 °C / Inert atmosphere
2: Inert atmosphere
3: thionyl chloride / benzene / 2 h / Reflux
4: 0 - 20 °C / Inert atmosphere
5: sec.-butyllithium / cyclohexane / 1 h / -78 °C / Inert atmosphere
6: boron tribromide / dichloromethane / 5.5 h / -78 - 25 °C / Inert atmosphere
7: dichloromethane / 20 h / 20 °C / Inert atmosphere
8: potassium carbonate / N,N-dimethyl-formamide / 20 h / 80 °C / Inert atmosphere
9: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; tert-butyl alcohol; water / 12 h / Inert atmosphere
10: sodium periodate / methanol / 1 h / 20 °C / Inert atmosphere
11: phenylborondichloride; N-ethyl-N,N-diisopropylamine / dichloromethane; methanol / 3.5 h / -78 °C / Inert atmosphere
12: benzo[1,3,2]dioxaborole / tetrahydrofuran / 20 h / -78 - 0 °C / Inert atmosphere
13: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 °C / Inert atmosphere
14: water; ethanol / 1.33 h / Reflux
15: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1 h / 20 °C / Inert atmosphere
With
2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; thionyl chloride; phenylborondichloride; sec.-butyllithium; boron tribromide; potassium carbonate; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; benzo[1,3,2]dioxaborole;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;
DOI:10.1021/ja3057612