Multi-step reaction with 12 steps
1: 93 percent / Mg / tetrahydrofuran / Heating
2: 99 percent / K2OsO2(OH)2; K2CO3; K3Fe(CN)6 / 2-methyl-propan-2-ol; H2O / 20 °C
3: 95 percent / 2,2-dimethoxypropane; PPTS / 20 °C
4: 99 percent / hydrogen / 10 percent Pd/C / ethyl acetate / 20 °C
5: 87 percent / NBS / dimethylformamide / 20 °C
6: 76 percent / NaH / dimethylformamide / 90 °C
7: 95 percent / NaBH4 / methanol; tetrahydrofuran / 20 °C
8: 90 percent / Ph3P; I2; imidazole / 20 °C
9: 85 percent / diethyl ether / 20 °C
10: 85 percent / BuONO; NaOMe / methanol / 0 °C
11: 87 percent / NaH / dimethylformamide / 20 °C
12: 85 percent / NBS / acetonitrile / 50 °C
With
1H-imidazole; sodium tetrahydroborate; N-Bromosuccinimide; n-Butyl nitrite; K2OsO2(OH)2; hydrogen; iodine; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; magnesium; triphenylphosphine; 2,2-dimethoxy-propane; potassium hexacyanoferrate(III);
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
1: Alkylation / 2: Oxidation / 3: acetonization / 4: Reduction / 5: Bromination / 6: Arylation / 7: Reduction / 8: Iodination / 9: Substitution / 10: Nitrosation / 11: Alkylation / 12: Bromination;
DOI:10.1016/S0040-4039(99)01429-X