Multi-step reaction with 15 steps
1.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 18 °C / Inert atmosphere
2.1: potassium carbonate / methanol / 1 h / 18 °C
3.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; benzene / 18 °C / Inert atmosphere; Reflux
4.1: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 18 h / 18 °C
5.1: potassium carbonate / methanol / 1 h / 18 °C
6.1: toluene / 168 h / Reflux
7.1: bromine / toluene / 18 h / 18 °C
7.2: 2 h
8.1: palladium 10% on activated carbon; hydrogen; potassium carbonate / methanol / 18 h / 18 °C
9.1: dmap / pyridine / 2 h / 18 °C
10.1: acetic acid / water / 20 h / 18 °C
11.1: dmap / dichloromethane / 1 h / 0 °C / Inert atmosphere
12.1: phosphorous acid trimethyl ester / toluene / 18 h / Reflux
13.1: potassium carbonate / methanol / 1 h / 18 °C
14.1: 1H-imidazole / dichloromethane / 18 h / 18 °C / Inert atmosphere
15.1: lithium triethylborohydride / tetrahydrofuran / 4 h / 18 °C / Inert atmosphere
With
1H-imidazole; dmap; tetrakis(triphenylphosphine) palladium(0); di-isopropyl azodicarboxylate; palladium 10% on activated carbon; hydrogen; bromine; lithium triethylborohydride; sodium carbonate; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; phosphorous acid trimethyl ester;
In
tetrahydrofuran; pyridine; methanol; dichloromethane; water; toluene; benzene;
3.1: Suzuki-Miyaura cross-coupling / 4.1: Mitsunobu reaction / 12.1: Corey-Winter olefination reaction;
DOI:10.1071/CH10201