Multi-step reaction with 11 steps
1.1: 1H-imidazole; triphenylphosphine; iodine / dichloromethane / 2 h / Cooling with ice; Inert atmosphere
2.1: caesium carbonate / N,N-dimethyl-formamide / 0.5 h / Cooling with ice; Inert atmosphere
2.2: 8 h / 20 °C / Inert atmosphere
2.3: 3.33 h / 20 °C / Inert atmosphere
3.1: C15H26Cl2CuN2O2; triethylamine / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere
4.1: Dess-Martin periodane / dichloromethane / 5 h / Cooling with ice; Inert atmosphere
5.1: dichloromethane / 15 h / 50 °C / Inert atmosphere
6.1: sodium hydrogencarbonate; mercuric triflate / dichloromethane / 10.5 h / -20 °C / Inert atmosphere; Cooling with ice
6.2: 0.5 h / -78 °C / Inert atmosphere
7.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 1 h / -78 °C / Inert atmosphere
8.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 10.33 h / -40 - -20 °C / Inert atmosphere
9.1: Trimethyl borate / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere
9.2: 3 h / 50 °C / Inert atmosphere
10.1: hydrogenchloride / methanol; water / 10 h / 40 °C / Inert atmosphere
11.1: N-ethyl-N,N-diisopropylamine / 0 °C / Inert atmosphere
11.2: 0 - 20 °C / Inert atmosphere
With
1H-imidazole; hydrogenchloride; Trimethyl borate; C15H26Cl2CuN2O2; iodine; mercuric triflate; diisobutylaluminium hydride; sodium hydrogencarbonate; caesium carbonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
4.1: |Dess-Martin Oxidation / 5.1: |Wittig Olefination;
DOI:10.1039/c3cc42365d