Multi-step reaction with 27 steps
1: 64 percent / dimethyldioxirane / acetone; CH2Cl2 / 40 h / Ambient temperature
2: 1.) tert-BuLi / 1.) pentane, THF, -78 deg C, 10 min, 2.) -78 deg C, 10 min
3: 88 percent / oxone, pH 4 aqueous buffer / tetrahydrofuran; methanol / 3.5 h / Ambient temperature
4: 80 percent / 15percent aq. H2SO4 / tetrahydrofuran / 12 h / 60 °C
5: 91 percent / imidazole / dimethylformamide / 1 h / Ambient temperature
6: 86 percent / NEt3 / CH2Cl2 / 0.25 h / Ambient temperature
7: 1.) DMSO, oxalyl chloride, 2.) NEt3 / 1.) THF, -35 deg C, 20 min, 2.) -78 deg C -> RT
8: 79 percent / NaBH4 / methanol / Ambient temperature
9: 1.) borane methyl sulphide complex, 2.) H2O2, NaOH / 1.) THF, RT, 64 h, 2.) 0 deg C -> RT
10: 84 percent / toluene-p-sulphonyl chloride, pyridine / 14 h / Ambient temperature
11: 1.) tert-BuLi / 1.) hexane, THF, -78 deg C, 10 min, 2.) -78 deg C, 10 min
12: 93 percent / 80percent m-chloroperbenzoic acid (mCPBA) / CH2Cl2 / 0.25 h / Ambient temperature
13: 80 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / acetonitrile / 3.5 h / Ambient temperature
14: 1.) tert-BuLi / 1.) pentane, THF, -78 deg C, 10 min, 2.) -78 deg C, 1 h
15: 34 percent / 6percent Na/Hg, Na2HPO4 / tetrahydrofuran; methanol / 2 h / -40 °C
16: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 36 h / Heating
17: tris(triphenylphosphine)ruthenium(II) chloride / benzene; CH2Cl2 / 48 h / Ambient temperature
18: 32 percent / NaClO2, 2-methylbut-2-ene / 2-methyl-propan-2-ol; H2O / 1 h / Ambient temperature
19: 47 percent / 2-chloro-1-methylpyridinium iodide, NEt3 / acetonitrile / 4 h / Heating
20: 61 percent / N-methylmorpholine N-oxide, tetrapropylammonium perruthenate / CH2Cl2 / 1 h / Ambient temperature
21: 88 percent / NEt3 / CH2Cl2 / 4 h / 0 °C
22: 44 percent / CH2Cl2 / 2 h / -78 °C
23: 87 percent / 40percent aq. HF, pyridine / acetonitrile / 36 h / Ambient temperature
24: 1.) 2-(phenylsulphonyl)-3-(p-nitrophenylsulphonyl)oxaziridine, 2.) NaBH4, CeCl3 / 1.) CHCl3, RT, 30 min, 2.) MeOH, 0 deg C, 15 min
25: 97 percent / pyridine, 4-dimethylaminopyridine (DMAP) / 1.5 h / Ambient temperature
26: 64 percent / AgClO4, CaCO3 / toluene / 0.17 h / Ambient temperature
27: 90 percent / LiBHEt3 / tetrahydrofuran / -78 °C
With
pyridine; 1H-imidazole; dmap; Oxone; sodium hydroxide; sodium chlorite; sodium tetrahydroborate; disodium hydrogenphosphate; sodium amalgam; cerium(III) chloride; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; oxalyl dichloride; tris(triphenylphosphine)ruthenium(II) chloride; dimethylsulfide borane complex; 2-(phenylsulphonyl)-3-(p-nitrophenylsulphonyl)oxaziridine; pH 4 aqueous buffer; sulfuric acid; hydrogen fluoride; tetrabutyl ammonium fluoride; 2-chloro-1-methyl-pyridinium iodide; dihydrogen peroxide; tert.-butyl lithium; silver perchlorate; 3,3-dimethyldioxirane; lithium triethylborohydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; calcium carbonate;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; tert-butyl alcohol; benzene;