Multi-step reaction with 11 steps
1.1: 100 percent / DIBALH / CH2Cl2; hexane / 6 h / 0 °C
2.1: 85 percent / I2; PPh3; imidazole / benzene / 0.33 h / 20 °C
3.1: 95 percent / potassium t-butoxide / tetrahydrofuran / 0.25 h / 0 °C
4.1: 9-BBN / tetrahydrofuran / 3 h / 20 °C
4.2: Pd(PPh3)4; aq. NaHCO3 / dimethylformamide; tetrahydrofuran / 19 h / 20 °C
5.1: BH3*SMe2 / tetrahydrofuran / 3 h / 20 °C
5.2: 338.0 mg / aq. H2O2; NaOH / tetrahydrofuran / 1 h / 20 °C
6.1: 86 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 20 °C
7.1: 85 percent / DDQ; aq. phosphate buffer / CH2Cl2 / 1.5 h / 20 °C / pH 7
8.1: 82 percent / N-methylmorpholine-N-oxide; tetra-n-propylammonium perruthenate; 4A molecular sieves / CH2Cl2 / 1 h / 20 °C
9.1: LHMDS; Et3N / tetrahydrofuran / 0.5 h / -78 °C
10.1: 181.8 mg / N-methylmorpholine-N-oxide; aq. OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol / 21 h / 20 °C
11.1: 100 percent / 2,6-lutidine / CH2Cl2 / 2 h / 20 °C
With
1H-imidazole; 2,6-dimethylpyridine; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; phosphate buffer; tetrapropylammonium perruthennate; dimethylsulfide borane complex; 4 A molecular sieve; potassium tert-butylate; iodine; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane;
In
tetrahydrofuran; hexane; dichloromethane; tert-butyl alcohol; benzene;
4.2: Suzuli-Miyaura cross-coupling;
DOI:10.1021/ja042686r