Multi-step reaction with 12 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere
1.2: 1 h / -78 °C / Inert atmosphere
2.1: toluene / 4.5 h / 120 °C / Inert atmosphere
3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere
3.2: -78 °C / Inert atmosphere
4.1: Crabtree's catalyst; hydrogen / dichloromethane / 48 h / 20 °C / Inert atmosphere
5.1: trimethylaluminum / hexane; dichloromethane / 0.5 h / 0 °C / Inert atmosphere
5.2: 1 h / 0 °C / Inert atmosphere
6.1: tert.-butyl lithium / tetrahydrofuran; diethyl ether; pentane / 0.67 h / -78 °C / Inert atmosphere
6.2: 1.5 h / Inert atmosphere
7.1: zinc(II) chloride / dichloromethane / 0 - 20 °C / Inert atmosphere
8.1: lithium aluminium tetrahydride / diethyl ether / 0.25 h / 0 °C / Inert atmosphere
9.1: sodium hydride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
10.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / 0 °C / Inert atmosphere
10.2: 0.08 h / 0 °C / Inert atmosphere
11.1: 0.5 h / 0 °C / Inert atmosphere
12.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 0.5 h / 90 °C / Inert atmosphere
With
lithium aluminium tetrahydride; n-butyllithium; Crabtree's catalyst; 2,2'-azobis(isobutyronitrile); hydrogen; trimethylaluminum; tert.-butyl lithium; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; sodium hydride; N-ethyl-N,N-diisopropylamine; zinc(II) chloride;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; pentane;
7.1: Diels-Alder reaction;
DOI:10.1248/cpb.60.137