Multi-step reaction with 13 steps
1.1: sodium hydride / tetrahydrofuran; paraffin oil / 0 °C
1.2: 6 h / 20 °C
2.1: ozone / dichloromethane / 0.25 h / -78 °C
2.2: -78 °C
3.1: sodium tetrahydroborate / methanol / 0 - 20 °C
4.1: 1H-imidazole / dichloromethane / 0 - 20 °C
5.1: copper(II) choride dihydrate / acetonitrile / 0 - 20 °C
6.1: di(n-butyl)tin oxide; triethylamine / dichloromethane / 0.5 h / 20 °C
7.1: potassium carbonate / methanol / 1 h / 20 °C
8.1: magnesium / diethyl ether
8.2: 2 h / -40 - 20 °C
9.1: sodium hydride / tetrahydrofuran; paraffin oil / 0.5 h / 0 °C
9.2: 5 h / 20 °C
10.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 20 °C
11.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
12.1: methanol; potassium carbonate / 2 h / 20 °C
13.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C
13.2: 5 h / 0 - 20 °C
With
1H-imidazole; methanol; sodium tetrahydroborate; copper(II) choride dihydrate; di-isopropyl azodicarboxylate; water; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; ozone; magnesium; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; paraffin oil;
11.1: Mitsunobu reaction;
DOI:10.1016/j.tetasy.2012.02.009