Multi-step reaction with 17 steps
1.1: triethylamine / dichloromethane / 3 h / -78 °C / Inert atmosphere
2.1: ozone / dichloromethane / 3 h / -78 °C
2.2: 4 h / 20 °C / Inert atmosphere
3.1: methanol; diethyl ether; toluene / 0.25 h / Inert atmosphere
4.1: lithium aluminium tetrahydride / tetrahydrofuran; dichloromethane / 0.5 h / 0 °C / Inert atmosphere
5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere
5.2: 16 h / 20 °C / Inert atmosphere
6.1: toluene-4-sulfonic acid / water; acetone / 0.5 h / 20 °C
7.1: triethylamine / dichloromethane / 0.75 h / 0 °C / Inert atmosphere
8.1: oxygen; palladium diacetate / dimethyl sulfoxide / 16 h / 20 - 80 °C
9.1: iodine; magnesium / tetrahydrofuran / 2 h / 70 °C / Inert atmosphere
9.2: 0.5 h / -78 °C / Inert atmosphere
9.3: 5 h / -78 °C / Inert atmosphere
10.1: toluene-4-sulfonic acid / acetone / 0.5 h / 20 °C / Inert atmosphere
11.1: n-butyllithium; lithium diisopropyl amide / tetrahydrofuran; cyclohexane / 1 h / -78 °C / Inert atmosphere
11.2: 3 h / -78 °C / Inert atmosphere
12.1: pyridine; dihydrogen peroxide / dichloromethane; water / 0.5 h / 0 - 20 °C
13.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.25 h / -78 °C / Inert atmosphere
14.1: 1,2-dichloro-benzene / 1 h / 220 °C / Microwave irradiation; Inert atmosphere
15.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
15.2: 0.5 h / -78 - 20 °C / Inert atmosphere
16.1: water; iodine / tetrahydrofuran / 16 h / 20 °C
17.1: triethyl borane; tri-n-butyl-tin hydride / hexane; toluene / 1 h / -78 °C / Air
With
pyridine; lithium aluminium tetrahydride; n-butyllithium; triethyl borane; water; dihydrogen peroxide; iodine; oxygen; tri-n-butyl-tin hydride; palladium diacetate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; magnesium; triethylamine; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; cyclohexane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 1,2-dichloro-benzene; acetone; toluene; mineral oil;
DOI:10.1002/ejoc.201101629