Multi-step reaction with 12 steps
1: 98 percent / LiAlH4 / diethyl ether / 1.) -50 deg C, 5h, 2.) RT, 18h
2: 1.) 2,2'-bipyridyl, 1.6M n-butyllithium / 1.) THF, hexane, 10 min, 2.) THF, RT, 15 min then 1h, reflux
3: 60 percent / m-chloroperbenzoic acid / CH2Cl2 / 4 h / 25 °C
4: 56 percent / NaBH4 / ethanol / 1.5 h / Heating
5: 87 percent / diisopropylamine, 85percent m-chloroperbenzoic acid / CH2Cl2 / 1 h / -78 °C
6: 1.) osmium tetraoxide, 2.) sodium bisulfite, H2O, pyridine / 1.) pyridine, 20h, RT, 2.) 3h
7: 87 percent / (+)-10-camphorsulfonic acid / cyclopentane / 3 h / 50 °C
8: 1.) 60percent NaH, imidazole / 1.) THF, oil, 2h, 60 deg C, 2.) 1h, 50 deg C
9: 86 percent / 0.5 h / Ambient temperature
10: 95 percent / tri-n-butyltin hydride / toluene / 1.) 20h, reflux, 2.) 50 deg C, 15 mmHg
11: 90 percent / 0.2M Ba(OH)2 / methanol / 6 h / Heating
12: 95 percent / 1N aq. HCl / tetrahydrofuran / 1 h / 25 °C
With
pyridine; 1H-imidazole; hydrogenchloride; [2,2]bipyridinyl; barium dihydroxide; sodium tetrahydroborate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; water; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogensulfite; (+)-10-camphorsulfonic acid; diisopropylamine; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; Cyclopentane; toluene;
DOI:10.1016/S0040-4020(01)87737-1