Multi-step reaction with 15 steps
1: 63 percent / benzene; diethyl ether / 6 h / Irradiation
2: 80 percent / NaHCO3 / CH2Cl2
3: 3 N HCl / tetrahydrofuran
4: MgSO4 / CH2Cl2
5: tetrahydrofuran / 48 h / Ambient temperature
6: CuSO4, CSA
7: 98 percent / Li, NH3 / diethyl ether
8: 1) o-NO2C6H4SeCN, Bu3P, 2) H2O2 / 1) THF, 2) THF
9: O3, NaHCO3 / CH2Cl2; methanol / -78 °C
10: Me2S / CH2Cl2; methanol / 3 h / Ambient temperature
11: 185 mg / 1.9 M n-BuLi/hexane / tetrahydrofuran / 0.67 h / -78 °C
12: 77 percent / camphorsulfonic acid / CH2Cl2 / 8 h / Ambient temperature
13: 1) CF3CO2COCH3, 2,6-lutidine, 2) CaCO3, HgCl2 / 1) Ac2O, r.t., 1 h, 2) MeCN, H2O, r.t., 2 h
14: 80 percent / LDA-HMPA / tetrahydrofuran / 0.25 h / -78 °C
15: 82 percent / p-toluenesulfonyl chloride, 4-dimethylaminopyridine, Et3N / CH2Cl2 / 12 h
With
2,6-dimethylpyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; ortho-nitrophenyl selenocyanate; dimethylsulfide; hexane; tributylphosphine; trifluoroacetic anhydride; camphor-10-sulfonic acid; ammonia; dihydrogen peroxide; lithium; sodium hydrogencarbonate; magnesium sulfate; ozone; copper(II) sulfate; triethylamine; p-toluenesulfonyl chloride; calcium carbonate; mercury dichloride; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene;
DOI:10.1021/ja00327a020