Multi-step reaction with 10 steps
1.1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide; mineral oil / 5 h / 0 - 20 °C / Inert atmosphere
2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1.5 h / 0 °C / Inert atmosphere
3.1: dirhodium tetraacetate / benzene / 1 h / Inert atmosphere; Reflux
4.1: indium(III) triflate; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 3 h / Inert atmosphere; Reflux
5.1: water; osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran / 7 h / 20 - 70 °C / Inert atmosphere
6.1: lithium hydroxide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
7.1: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran; dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
7.2: 1 h / -78 °C / Inert atmosphere
8.1: water; toluene-4-sulfonic acid / acetone / 12.5 h / 20 °C / Inert atmosphere; Reflux
9.1: diisobutylaluminium hydride / hexane; toluene / 1 h / -78 °C / Inert atmosphere
10.1: n-butyllithium / hexane; dimethyl sulfoxide / 2 h / 20 - 200 °C / Inert atmosphere
10.2: 4 h / 20 - 120 °C / Inert atmosphere
With
indium(III) triflate; dirhodium tetraacetate; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; water; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N,N-dimethyl-formamide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hydroxide;
In
tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; mineral oil; benzene;
DOI:10.1021/jo400263w