Multi-step reaction with 13 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 - -55 °C / Inert atmosphere
1.2: 0.5 h / -78 °C / Inert atmosphere
1.3: 0.33 h / -78 °C / Inert atmosphere
2.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 5 h / 20 °C / Inert atmosphere
3.1: pyridinium p-toluenesulfonate / methanol / 22 h / 40 °C / Inert atmosphere
4.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere
5.1: tetrahydrofuran / -78 °C / Inert atmosphere
5.2: 1 h / 20 °C / Molecular sieve; Inert atmosphere
6.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere
6.2: 0.83 h / -78 °C / Inert atmosphere
7.1: magnesium bromide diethyl etherate / dichloromethane / -78 - 0 °C / Inert atmosphere
8.1: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 h / 35 °C / Inert atmosphere
9.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 0 - 20 °C / pH 7 / aq. buffer; Inert atmosphere
10.1: Zeise's dimer / diethyl ether / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere
11.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 0 - 20 °C
12.1: pyridinium p-toluenesulfonate / dichloromethane / 1.5 h / 20 °C / Inert atmosphere
13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 35 °C / Inert atmosphere
With
n-butyllithium; tetrapropylammonium perruthennate; magnesium bromide diethyl etherate; Zeise's dimer; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1021/ol301795a