Multi-step reaction with 12 steps
1.1: 4.82 g / benzene / 0 - 20 °C
2.1: sec-BuLi; CuBr*Me2S / tetrahydrofuran; cyclohexane / -78 - -15 °C
2.2: 76 percent / tetrahydrofuran; cyclohexane / 1 h / -78 °C
3.1: 81 percent / BBr3 / CH2Cl2 / 5.5 h / -78 - 25 °C
4.1: 73 percent / CH2Cl2 / 20 h / 20 °C
5.1: 92 percent / K2CO3; Bu4NI / dimethylformamide / 20 h / 80 °C
6.1: 4-methylmorpholine-N-oxide; aq. OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol / 12 h / 20 °C
7.1: 408 mg / aq. NaIO4 / methanol / 1 h / 20 °C
8.1: PhBCl2; diisopropylethylamine / CH2Cl2 / 2 h / -78 - 0 °C
8.2: CH2Cl2 / 3.5 h / -78 °C
9.1: catecholborane / tetrahydrofuran / 0 °C
10.1: aq. NaOH / tetrahydrofuran / 0.5 h / 20 °C
11.1: TBAF / tetrahydrofuran / 2 h / 20 °C
12.1: PtH(PMe2OH)(PMe2O)2H; H2O / ethanol / 1.33 h / Heating
With
sodium hydroxide; sodium periodate; osmium(VIII) oxide; copper(I) bromide dimethylsulfide complex; (Me2PO)2HPt(Me2POH); phenylborondichloride; tetrabutyl ammonium fluoride; water; sec.-butyllithium; boron tribromide; tetra-(n-butyl)ammonium iodide; potassium carbonate; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; benzo[1,3,2]dioxaborole;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; cyclohexane; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;
DOI:10.1021/ja0537068