Multi-step reaction with 13 steps
1.1: n-butyllithium / hexane; tetrahydrofuran / -78 °C
1.2: -78 °C
2.1: hydrogen; quinoline / Lindlar catalyst / ethyl acetate / 0.67 h
3.1: diethylzinc / dichloromethane; diethyl ether / -20 °C / Inert atmosphere
3.2: 0.17 h / -20 °C / Inert atmosphere
3.3: 24 h / -20 - 0 °C / Inert atmosphere
4.1: hydrogen / 20 % Pd(OH)2/C / ethyl acetate; ethanol / 0.5 h / 2585.81 Torr
5.1: sodium periodate / dichloromethane; water / 0 °C
6.1: ethanol; sodium tetrahydroborate / 0.5 h / 20 °C
7.1: trifluoroacetic acid / dichloromethane / 0 °C
8.1: caesium carbonate / N,N-dimethyl-formamide / 6 h / 20 °C
9.1: triethylamine / dmap / dichloromethane / 1.5 h / Inert atmosphere
10.1: sodium azide / 1,4-dioxane; water / 2 h / 100 °C
11.1: triphenylphosphine; water / tetrahydrofuran / 2 h / 20 - 40 °C
12.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 1-methyl-pyrrolidin-2-one / 0.08 h / 20 °C
12.2: 17 h / 20 - 110 °C
13.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C
With
quinoline; sodium tetrahydroborate; sodium periodate; n-butyllithium; sodium azide; ethanol; water; hydrogen; diethylzinc; sodium tris(acetoxy)borohydride; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; trifluoroacetic acid;
dmap; 20 % Pd(OH)2/C;
In
tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; diethyl ether; ethanol; hexane; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
3.1: Charette cyclopropanation;