Multi-step reaction with 10 steps
1.1: di-n-butylboryl trifluoromethanesulfonate; triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
1.2: 3 h / -78 °C / Inert atmosphere
2.1: trimethylaluminum / toluene; tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
2.2: 1 h / -20 - 0 °C / Inert atmosphere
3.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
4.1: diisobutylaluminium hydride / toluene; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
5.1: lithium tert-butoxide / hexane; dichloromethane / 20 °C / Inert atmosphere
6.1: tetrakis(triphenylphosphine) palladium(0); copper(I) thiophene-2-carboxylate / benzene / 18 h / 65 - 125 °C / Darkness; Inert atmosphere; Schlenk technique
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 55 °C / Molecular sieve; Inert atmosphere
8.1: diisobutylaluminium hydride / dichloromethane; toluene / 1.5 h / -78 °C / Inert atmosphere
9.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
10.1: sodium hydrogencarbonate; tert-butyl alcohol; Dess-Martin periodane / dichloromethane / 0.08 h / Inert atmosphere
With
1H-imidazole; 2,6-dimethylpyridine; tetrakis(triphenylphosphine) palladium(0); copper(I) thiophene-2-carboxylate; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; trimethylaluminum; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; lithium tert-butoxide; tert-butyl alcohol;
In
tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
6.1: |Diels-Alder Cycloaddition;
DOI:10.1021/ol400508s