Multi-step reaction with 12 steps
1.1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C
1.2: 3 h / 20 °C
2.1: boron trifluoride diethyl etherate / tetrahydrofuran / 1 h / 20 °C
3.1: titanium tetrachloride / dichloromethane / 0.17 h / 0 °C
3.2: 0.5 h / 0 °C
3.3: 3.5 h / -78 - 0 °C
4.1: 1H-imidazole / dichloromethane / 24 h / 20 °C
5.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C
6.1: tetrahydrofuran / 0 °C
7.1: n-butyllithium / tetrahydrofuran; hexane / 0.58 h / 0 - 20 °C
7.2: 0 - 20 °C
8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 20 °C
9.1: di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; triphenylphosphine / tetrahydrofuran / 12 h / 0 °C
10.1: water; triphenylphosphine / tetrahydrofuran / 12 h / 45 °C
11.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
12.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 24 h / Inert atmosphere; Reflux
With
1H-imidazole; sodium tetrahydroborate; n-butyllithium; Hoveyda-Grubbs catalyst second generation; di-isopropyl azodicarboxylate; diphenyl phosphoryl azide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; titanium tetrachloride; triethylamine; triphenylphosphine;
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
3.3: Evans syn aldol reaction / 7.2: Wittig reaction / 10.1: Staudinger reaction;
DOI:10.1055/s-0031-1291047