Multi-step reaction with 8 steps
1.1: sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 1.5 h / 0 °C / Inert atmosphere
2.1: titanium tetrachloride / toluene / 1.17 h / -78 °C / Inert atmosphere
2.2: 3.5 h / -78 - 5 °C
3.1: 1,1,1,3,3,3-hexamethyl-disilazane; sodium iodide / acetonitrile / 3 h / 82 °C / Inert atmosphere
4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 3 h / 23 °C / Inert atmosphere
5.1: diethylzinc / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere
5.2: 0.67 h / -78 - 0 °C / Inert atmosphere
5.3: 0.42 h / -78 - -20 °C / Inert atmosphere
6.1: cerium(III) chloride; lithium chloride / diethyl ether / 3.25 h / -78 °C / Inert atmosphere
6.2: 2 h / -78 - 0 °C / Inert atmosphere
7.1: pyridinium p-toluenesulfonate / benzene / 4.5 h / 23 °C / Inert atmosphere
8.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 7 h / -78 - -5 °C / Inert atmosphere
With
cerium(III) chloride; diethylzinc; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; titanium tetrachloride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; lithium chloride;
In
tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; toluene; acetonitrile; benzene;
1.1: Parikh-Doering oxidation / 2.1: Diels-Alder reaction / 2.2: Diels-Alder reaction;
DOI:10.1021/ol202728v