Multi-step reaction with 12 steps
1.1: n-butyllithium / hexane; tert-butyl methyl ether / 0.17 h / -78 °C / Inert atmosphere
1.2: 0.67 h / 0 - 20 °C / Inert atmosphere
2.1: sodium hydride / hexane / 2 h / Inert atmosphere; Reflux
3.1: acetylacetonatodicarbonylrhodium(l) / benzene / 4.5 h / 60 °C / 51716.2 Torr / Autoclave
3.2: 1 h / 40 °C / Inert atmosphere
4.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 °C / Inert atmosphere
5.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / -78 °C / Inert atmosphere
5.2: -78 - 20 °C / Inert atmosphere
6.1: toluene / 18 h / Inert atmosphere; Reflux
7.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; citric acid / tetrahydrofuran; tert-butyl alcohol / 24 h / Inert atmosphere
8.1: sodium periodate; sodium hydrogencarbonate / tetrahydrofuran; water / 1 h / 0 °C / Inert atmosphere
9.1: tetra-(n-butyl)ammonium iodide / dichloromethane; water / 3 h / Inert atmosphere
10.1: acetylacetonatodicarbonylrhodium(l); hydrogen; triphenylphosphine / tetrahydrofuran / 24 h / 20 - 50 °C / 25858.1 Torr / Autoclave
11.1: pyridine; dmap / dichloromethane / 16 h / -20 °C / Inert atmosphere
12.1: titanium tetrachloride / dichloromethane / 0.08 h / 0 °C / Inert atmosphere
12.2: 3 h / -40 °C / Inert atmosphere
With
pyridine; 2,6-dimethylpyridine; dmap; acetylacetonatodicarbonylrhodium(l); sodium periodate; osmium(VIII) oxide; n-butyllithium; water; hydrogen; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; triphenylphosphine; citric acid;
In
tetrahydrofuran; hexane; dichloromethane; tert-butyl methyl ether; water; toluene; tert-butyl alcohol; benzene;
9.1: Felkin addition;
DOI:10.1021/ja201467z