Multi-step reaction with 15 steps
1.1: 92 percent / H2SO4 / Heating
2.1: H2 / Pd/C / ethanol / 20 °C
2.2: 78 percent / NaNO2; H2SO4 / Heating
3.1: 83 percent / Br2 / CH2Cl2 / -45 °C
4.1: 92 percent / imidazole / dimethylformamide / 20 °C
5.1: 95 percent / diisobutylaluminum hydride / CH2Cl2 / -78 °C
6.1: 90 percent / PPTS / CH2Cl2 / 20 °C
7.1: n-BuLi / tetrahydrofuran / -78 °C
8.1: NaH / tetrahydrofuran / 20 °C
9.1: 73 percent / CBr4; PPh3 / CH2Cl2 / 40 °C
10.1: t-BuLi / diethyl ether / -78 °C
10.2: PPh3 / Pd2(dba)3 / dimethylformamide / 30 °C
11.1: 85 percent / 1,3-propanedithiol; BF3*OEt2 / CH2Cl2 / -78 °C
12.1: imidazole / dimethylformamide / 0 °C
13.1: DIBALH / CH2Cl2 / -78 °C
14.1: MnO2 / CH2Cl2 / 20 °C
15.1: NaClO2; NaH2PO4; 2-methyl-2-butene / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 20 °C
With
1H-imidazole; 1.3-propanedithiol; manganese(IV) oxide; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; carbon tetrabromide; sulfuric acid; boron trifluoride diethyl etherate; hydrogen; bromine; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; triphenylphosphine;
palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
2.2: Sandmeyer reaction / 8.1: Horner-Wadsworth-Emmons reaction / 10.2: Stille reaction / 15.1: Pinnic oxidation;
DOI:10.1016/j.tetlet.2007.05.174