Multi-step reaction with 9 steps
1.1: 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere; Cooling with water bath
2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -90 - -80 °C / Inert atmosphere
2.2: 0.5 h / -100 - -10 °C / Inert atmosphere
3.1: dichloromethane / 20 °C / Inert atmosphere
4.1: hydroquinidine 1 4-phthalazinediyl diether; potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; water; potassium carbonate; potassium hexacyanoferrate(III) / tert-butyl alcohol / 0 - 20 °C / Inert atmosphere
5.1: hydrogen azide; triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / -25 - 20 °C / Inert atmosphere
6.1: proton sponge / 1,2-dichloro-ethane / 40 °C / Inert atmosphere
7.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C
8.1: benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / -10 - 20 °C / Inert atmosphere
9.1: water; sodium hydroxide / tetrahydrofuran; methanol / 20 °C / Inert atmosphere
9.2: pH Ca. 2
With
1H-imidazole; hydroquinidine 1 4-phthalazinediyl diether; n-butyllithium; hydrogen azide; potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; palladium 10% on activated carbon; water; hydrogen; potassium carbonate; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium hydroxide; potassium hexacyanoferrate(III); diethylazodicarboxylate;
In
tetrahydrofuran; methanol; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
2.2: Wittig reaction / 3.1: Wittig reaction / 4.1: Sharpless dihydroxylation / 5.1: Mitsunobu reaction;
DOI:10.1002/chem.201101978