Multi-step reaction with 10 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran; toluene / 0.17 h / 0 - 20 °C / Inert atmosphere
1.2: 0.67 h / 20 °C / Inert atmosphere
2.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / dichloromethane / 1.5 h / 20 °C / Inert atmosphere
3.1: sodium periodate; sodium hydrogencarbonate / dichloromethane; water / 20 °C / Inert atmosphere
4.1: sodium tetrahydroborate / methanol / 0.17 h / 0 °C / Inert atmosphere
5.1: Crabtree's catalyst; hydrogen / dichloromethane / 0 °C / Inert atmosphere
6.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere
7.1: methanol; potassium carbonate / 2 h / 20 °C / Inert atmosphere
8.1: pyridinium p-toluenesulfonate / dichloromethane / 2 h / 20 °C / Inert atmosphere
9.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C / Inert atmosphere
9.2: 0 - 20 °C / Inert atmosphere
10.1: water; dihydrogen peroxide; sodium hydroxide / tetrahydrofuran; hexane / 0.5 h / 20 °C / Inert atmosphere
With
1H-imidazole; methanol; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; n-butyllithium; Crabtree's catalyst; water; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; 4-methylmorpholine N-oxide; sodium hydroxide; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol300672q