Multi-step reaction with 9 steps
1: 1.) 18-crown-6, O2, 2.) potassium hexamethyldisilazide / 1.) THF, 30 min, 2.) THF, toluene, 0 deg C, 10 min
2: 65 percent / lithium aluminum hydride / diethyl ether / 0.5 h / 25 °C
3: 85 percent / 4-(dimethylamino)pyridine, pyridine / 25 °C
4: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 3 min, 2.) THF, from -78 deg C to RT, 1 h
5: 92 percent / 30percent aq. H2O2, AcOH / tetrahydrofuran / 1 h / 0 °C
6: 82 percent / SmI2 / tetrahydrofuran; methanol / -78 °C
7: 1.) pyridine, OsO4, 2.) aq. NaHSO3 / 1.) THF, -18 deg C, 2 h, 2.) THF, overnight
8: 100 percent / camphorsulfonic acid / dimethylformamide / 6 h / 50 - 55 °C
9: 93 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 0 °C
With
pyridine; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; samarium diiodide; 18-crown-6 ether; camphor-10-sulfonic acid; dihydrogen peroxide; oxygen; potassium hexamethylsilazane; sodium hydrogensulfite; acetic acid; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/ja980538t