Multi-step reaction with 8 steps
1.1: potassium tert-butylate / toluene / 0.33 h / 20 °C / Inert atmosphere
1.2: 4 h / 70 °C / Inert atmosphere
2.1: trifluoroacetic acid / acetonitrile; water / 1 h / 20 °C
3.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 0.33 h / Cooling with ice
3.2: 3 h / 20 °C
4.1: hydrogen; 20% palladium hydroxide-activated charcoal / ethanol / 20 °C
5.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 1 h / 0 °C
6.1: diamide; tributylphosphine / tetrahydrofuran / 60 °C
7.1: hydrogenchloride / ethyl acetate / 20 °C
8.1: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,2-dimethoxyethane / 9 h / 60 °C
With
hydrogenchloride; tris-(dibenzylideneacetone)dipalladium(0); tributylphosphine; diamide; 20% palladium hydroxide-activated charcoal; potassium tert-butylate; hydrogen; sodium hydride; diisobutylaluminium hydride; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; trifluoroacetic acid; sodium t-butanolate;
In
tetrahydrofuran; 1,2-dimethoxyethane; ethanol; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil;
1.1: |Wittig Olefination / 1.2: |Wittig Olefination / 3.1: |Horner-Wadsworth-Emmons Olefination / 3.2: |Horner-Wadsworth-Emmons Olefination / 6.1: |Mitsunobu Displacement;
DOI:10.1016/j.bmc.2018.02.032