Multi-step reaction with 9 steps
1: 60 percent / DABCO, BuLi / tetrahydrofuran; hexane / -78 °C
2: 80 percent / baker's yeast / H2O; ethanol / 48 h / Ambient temperature
3: 67 percent / vanadium(IV)oxy acetylacetonate, t-BuOOH / CH2Cl2 / 7 h / -20 °C
4: 1.) Et3N, Ms2O, 2.) DBU / 1.) CH2Cl2, 0 deg C, 10 min, 2.) RT, 30 min
5: (Me3Si)2NH, BuLi / tetrahydrofuran; hexane / 1.) -30 deg C, 2 h, 2.) -78 deg C, 1 h
6: 78 percent / activated zinc powder / acetic acid / 24 h / Ambient temperature
7: 77 percent / NaH, KH / tetrahydrofuran / 4.5 h / Heating
8: 72 percent / NaBH4 / propan-2-ol / 2.5 h / -10 - 20 °C
9: 63 percent / 1.) methanesulfonyl chloride, Et3N, 4-dimethylaminopyridine, 2.) DBU / CH2Cl2 / 1.5 h / 0 - 20 °C
With
1,4-diaza-bicyclo[2.2.2]octane; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; n-butyllithium; baker's yeast; potassium hydride; sodium hydride; vanadyl acetylacetonate; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; zinc; Methanesulfonic anhydride;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; water; acetic acid; isopropyl alcohol;
DOI:10.1055/s-1994-25674