Multi-step reaction with 10 steps
1.1: n-butyllithium; potassium tert-butylate / tetrahydrofuran; hexane / 0.25 h / -40 °C / Inert atmosphere
1.2: 0.5 h / -78 °C / Inert atmosphere
1.3: 2 h / -78 °C / Inert atmosphere
2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 4 °C
2.2: 0.25 h / 20 °C
3.1: iodine(I) bromide / dichloromethane; toluene / 2 h / -78 °C
3.2: 0.75 h / 20 °C
4.1: methanol; sodium methylate / 2 h / 20 - 50 °C
5.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 55 h / 20 °C
6.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / 20 °C / Inert atmosphere
6.2: 18 h / 4 °C / Inert atmosphere
7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 20 °C / Inert atmosphere; Molecular sieve
8.1: pyridinium p-toluenesulfonate / methanol; dichloromethane / 1.5 h / 20 °C
9.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.33 h / 20 °C / Molecular sieve
10.1: (S)-[1,1']-binaphthalenyl-2,2'-diol; titanium(IV)isopropoxide; titanium tetrachloride; silver(l) oxide / dichloromethane / 63 h / -15 °C
With
methanol; n-butyllithium; tetrapropylammonium perruthennate; potassium tert-butylate; sodium methylate; (S)-[1,1']-binaphthalenyl-2,2'-diol; sodium hexamethyldisilazane; titanium(IV)isopropoxide; pyridinium p-toluenesulfonate; iodine(I) bromide; titanium tetrachloride; sodium hydride; 4-methylmorpholine N-oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; silver(l) oxide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;
DOI:10.1021/jm300566h