Multi-step reaction with 9 steps
1.1: 95 percent / imidazole / dimethylformamide / 20 °C
2.1: LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 °C
2.2: 82 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 °C
3.1: 88 percent / 2,6-lutidine / CH2Cl2 / 1 h / -78 °C
4.1: 90 percent / camphorsulfonic acid / acetonitrile / 20 °C
5.1: 500 mg / Dess-Martin periodinane / CH2Cl2 / 20 °C
6.1: 301 mg / benzene / 3 h / 20 °C
7.1: 66 mg / H2 / Pd/C / ethyl acetate / 1 h / 20 °C
8.1: 57 mg / NaBH4 / methanol / 2 h / 20 °C
9.1: 95 percent / tributylphosphine / tetrahydrofuran / 3 h / 20 °C
With
1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; tributylphosphine; camphor-10-sulfonic acid; hydrogen; Dess-Martin periodane; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.3987/com-02-s46