Multi-step reaction with 14 steps
1.1: triethylamine; formic acid / palladium 10% on activated carbon / 120 h / 0 - 80 °C
2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C
2.2: 3 h / 0 °C
3.1: bromine; pyridine / dichloromethane / 2 h / 0 °C
4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 25 °C
6.1: copper(I) bromide; sodium / N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux
7.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane / 0.08 h / 0 °C
7.2: 12.25 h / 0 - 25 °C
8.1: lithium diisopropyl amide / tetrahydrofuran / 0.08 h / -78 °C
8.2: 1 h / -78 °C
9.1: Dess-Martin periodane / dichloromethane / 1 h / 25 °C
10.1: tetrahydrofuran / 1 h / 0 °C
11.1: sodium periodate / water; methanol / 8 h / 20 °C
12.1: potassium permanganate / water; methanol / 2 h / 20 °C
13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
14.1: hydrogen / palladium 10% on activated carbon / methanol / 6 h / 50 °C / 2585.81 Torr
With
pyridine; potassium permanganate; sodium periodate; formic acid; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; hydrogen; bromine; sodium; sodium hydride; Dess-Martin periodane; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(I) bromide; sodium hydroxide; lithium diisopropyl amide;
palladium 10% on activated carbon;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;