Multi-step reaction with 9 steps
1.1: N-iodo-succinimide / acetic acid / 2 h / 70 °C
2.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 60 °C
3.1: zinc; chloro-trimethyl-silane; ethylene dibromide / N,N-dimethyl-formamide / 1 h / 40 °C
3.2: 70 °C
4.1: sodium tetrahydroborate; methanol / 1 h / 0 - 20 °C
5.1: 1,3,5-trichloro-2,4,6-triazine; N,N-dimethyl-formamide / dichloromethane / 20 °C
6.1: caesium carbonate; potassium iodide / N,N-dimethyl-formamide / 3 h / 140 °C
7.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / N,N-dimethyl-formamide; water / 100 °C / Inert atmosphere
8.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide; water / tert-butyl alcohol / 20 °C
9.1: sodium periodate; acetic acid / water; tetrahydrofuran / 2 h / 0 °C
With
methanol; sodium tetrahydroborate; sodium periodate; N-iodo-succinimide; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium(0); chloro-trimethyl-silane; 1,3,5-trichloro-2,4,6-triazine; water; sodium carbonate; potassium carbonate; caesium carbonate; acetic acid; 4-methylmorpholine N-oxide; ethylene dibromide; N,N-dimethyl-formamide; potassium iodide; zinc;
In
tetrahydrofuran; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; tert-butyl alcohol;