Multi-step reaction with 10 steps
1.1: di-tert-butyl-diazodicarboxylate; triphenylphosphine / dichloromethane / 2.1 h / 0 - 20 °C / Inert atmosphere
2.1: potassium hydroxide / methanol / 0 °C
3.1: triethylamine / dichloromethane / -30 °C / Inert atmosphere
4.1: sodium azide / N,N-dimethyl-formamide / 50 °C / Inert atmosphere
5.1: triphenylphosphine / tetrahydrofuran; water / 0 - 50 °C / Inert atmosphere
6.1: dicyclohexyl-carbodiimide / dichloromethane / 0 - 20 °C / Inert atmosphere
7.1: ozone / methanol; dichloromethane / -78 °C / Inert atmosphere
7.2: -78 °C / Inert atmosphere
8.1: sodium tetrahydroborate / methanol; dichloromethane / -78 - -3 °C / Inert atmosphere
9.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
10.1: triethylamine; trichlorophosphate / dichloromethane / -30 °C / Inert atmosphere
With
1H-imidazole; sodium tetrahydroborate; sodium azide; di-tert-butyl-diazodicarboxylate; ozone; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; potassium hydroxide; trichlorophosphate;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1039/c1ob06632c