Multi-step reaction with 12 steps
1.1: 71 percent / p-TsOH*H2O; Na2SO4 / benzene / 5 h / 90 °C
2.1: 79 percent / LiN(TMS)2 / tetrahydrofuran; toluene / 1.17 h / -78 - 20 °C
3.1: 2,5-di-tert-butylhydroquinone / benzene / 56 h / 200 °C
4.1: p-TsOH*H2O / acetone / 0.5 h / 20 °C
5.1: 75 percent / p-cymene / Pd/C / 45 h / 200 °C
6.1: 97 percent / NaH / tetrahydrofuran / 2.5 h / 20 °C
7.1: 87 percent / NaBH4; NiCl2*6H2O / methanol / 3 h / 0 - 20 °C
8.1: 100 percent / pTsOH*H2O / benzene / 0.67 h / 20 - 100 °C
9.1: 86 percent / mCPBA; Mn(III) complex of (S,S)-1,2-cyclohexanediamine derivative; N-methylmorpholine N-oxide / CH2Cl2 / 1 h / -78 °C
10.1: H2SO4; acetonitrile / hexane / 1 h / 20 °C
10.2: 39 percent / H2O / 2 h / 100 °C
11.1: CHCl3 / 3 h / 24 °C
12.1: 1.12 g / LiAlH4 / diethyl ether; tetrahydrofuran / 0.08 h / 20 °C
With
sodium tetrahydroborate; lithium aluminium tetrahydride; 4-methylisopropylbenzene; Mn(III) complex of (S,S)-1,2-cyclohexanediamine derivative; sulfuric acid; 2,5-bis(1,1-dimethylethyl)-1,4-benzenediol; sodium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; sodium sulfate; 3-chloro-benzenecarboperoxoic acid; acetonitrile; nickel dichloride; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; chloroform; acetone; toluene; benzene;
3.1: Diels-Alder reaction / 9.1: Jacobsen reaction / 10.1: Ritter reaction;
DOI:10.1021/jo049381f