Multi-step reaction with 8 steps
1: 1) n-BuLi, TMEDA / 1) hexane, ether, RT, 2 h, 2) RT, 18 h
2: 60 percent / 0.5 N H2SO4 / tetrahydrofuran / 20 h
3: p-toluenesulfonic acid monohydrate / benzene / 20 h / Heating
4: 1) BH3, 2) 3N NaOH, 30 percent H2O2 / 1) THF, RT, overnight, 2a) 1 h, RT, 2b) 45 deg C, overnight
5: 88 percent / pyridinium chlorochromate / CH2Cl2
6: 1) NaH / 1) DME, 2) toluene, 36 h, reflux
7: 1) OsO4, 2) NaIO4 / 1) ether, water, 20 min, 2) 48 h
8: 90 percent / NaH, t-amyl alcohol / benzene / 0.5 h / Heating
With
sodium hydroxide; sodium periodate; osmium(VIII) oxide; n-butyllithium; tert-Amyl alcohol; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; borane; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate;
In
tetrahydrofuran; dichloromethane; benzene;
DOI:10.1021/jo00194a026