Multi-step reaction with 10 steps
1: p-TsOH / benzene / Heating
2: LiICA / CH2Cl2 / -78 °C
3: 30percent H2O2 aq. / CH2Cl2 / 0 °C
4: 1) OsO4, NaHSO3, 2) NaIO4 / 1) benzene, pyridine, room temp., 2) ether, room temp.
5: NaBH4 / ethanol / 0 °C
6: imidazole / dimethylformamide
7: p-TsOH / H2O; tetrahydrofuran / Heating
8: 75 percent / LDA / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 °C
10: 1) n-Bu3SnH, 2) n-BuLi / 1) AIBN / 1)80 deg C, 2) THF, -50 to -78 deg C, then 0 deg C
With
1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; n-butyllithium; dihydrogen peroxide; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; sodium hydrogensulfite; lithium diisopropyl amide;
2,2'-azobis(isobutyronitrile);
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(01)80292-6