Multi-step reaction with 7 steps
1: 65.9 percent / BH3*THF / tetrahydrofuran / 20 h / 4 °C
2: 89.4 percent / imidazole / dimethylformamide / 2 h
3: 1.) potassium bis(trimethylsilyl)amide / 1.) THF, toluene, -78 deg C, 3 min, 2.) THF, toluene, -78 deg C, 20 min
4: 92.7 percent / AcOH, H2O / tetrahydrofuran / 0.83 h / 50 °C
5: 1.) I2, Ph3P, imidazole / 1.) benzene, RT, 1 h, 2.) benzene, 60 deg C, 30 min
6: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 30percent aq. H2O2, 2N aq. NaOH / 1.) THF, 14 h, 2.) THF, 1 h
7: 100 percent / Ph3P, diethyl azodicarboxylate / tetrahydrofuran / 14 h / Ambient temperature
With
1H-imidazole; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; borane-THF; water; dihydrogen peroxide; iodine; potassium hexamethylsilazane; acetic acid; triphenylphosphine; diethylazodicarboxylate;
In
tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1248/cpb.43.1683