Multi-step reaction with 19 steps
1.1: phosphoric acid / 1 h / 18 °C
2.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 18 °C / Inert atmosphere
3.1: potassium carbonate / methanol / 1 h / 18 °C
4.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; benzene / 18 °C / Inert atmosphere; Reflux
5.1: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 18 h / 18 °C
6.1: potassium carbonate / methanol / 1 h / 18 °C
7.1: toluene / 168 h / Reflux
8.1: bromine / toluene / 18 h / 18 °C
8.2: 2 h
9.1: palladium 10% on activated carbon; hydrogen; potassium carbonate / methanol / 18 h / 18 °C
10.1: dmap / pyridine / 2 h / 18 °C
11.1: acetic acid / water / 20 h / 18 °C
12.1: dmap / dichloromethane / 1 h / 0 °C / Inert atmosphere
13.1: phosphorous acid trimethyl ester / toluene / 18 h / Reflux
14.1: potassium carbonate / methanol / 1 h / 18 °C
15.1: 1H-imidazole / dichloromethane / 18 h / 18 °C / Inert atmosphere
16.1: lithium triethylborohydride / tetrahydrofuran / 4 h / 18 °C / Inert atmosphere
17.1: Dess-Martin periodane / dichloromethane / 16 h / 18 °C
18.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 0.75 h / 95 °C
19.1: tetrahydrofuran; tetrachloromethane / 0.75 h / 95 °C
With
1H-imidazole; dmap; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium(0); 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; phosphoric acid; palladium 10% on activated carbon; hydrogen; bromine; lithium triethylborohydride; sodium carbonate; potassium carbonate; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; phosphorous acid trimethyl ester;
In
tetrahydrofuran; pyridine; methanol; tetrachloromethane; dichloromethane; water; toluene; benzene;
4.1: Suzuki-Miyaura cross-coupling / 5.1: Mitsunobu reaction / 13.1: Corey-Winter olefination reaction;
DOI:10.1071/CH10201