Multi-step reaction with 12 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C
2.1: pyridine; dmap / 5 h / 0 °C
3.1: pyridine; methanesulfonyl chloride / 5 h / 0 - 55 °C
4.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); cyclohexane-1,2-epoxide / tetrachloromethane / 10 h / 90 °C
5.1: methanol; potassium carbonate / 20 °C
6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 0 °C
7.1: toluene-4-sulfonic acid / dichloromethane / 4 h / 0 °C
8.1: n-butyllithium / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
8.2: -78 - 20 °C
9.1: bis-[(trifluoroacetoxy)iodo]benzene; calcium carbonate / dichloromethane; water; acetonitrile / 0.17 h / 0 °C
10.1: dmap; triethylamine / dichloromethane / 20 °C
11.1: oxygen; 5,15,10,20-tetraphenylporphyrin / dichloromethane / 3 h / -78 °C / UV-irradiation
12.1: acetic acid; zinc / tetrahydrofuran / 10 h / 20 °C
With
pyridine; methanol; dmap; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; 2,2'-azobis(isobutyronitrile); oxygen; 5,15,10,20-tetraphenylporphyrin; cyclohexane-1,2-epoxide; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; methanesulfonyl chloride; triethylamine; bis-[(trifluoroacetoxy)iodo]benzene; calcium carbonate; zinc;
In
tetrahydrofuran; tetrachloromethane; dichloromethane; water; acetonitrile;
DOI:10.1002/asia.201000882