Multi-step reaction with 12 steps
1: 93 percent / DIBAH / hexane / 1.) -60 deg C, 2.) RT, 1 h
2: 95 percent / PPTS / benzene / 23 h / Heating
3: 1.) Me2S*BH3, 3.) 30percent H2O2, 3N NaOH / 1.) ether, 0 deg C, 15 min, 2.) RT, 4 h, 3.) reflux, 1 h
4: 82 percent / CrO3, pyridine / CH2Cl2 / 0.25 h
5: 99 percent / H2O / PPTS / acetone / 48 h / Heating
6: 49 percent / BuLi / tetrahydrofuran; hexane / 0 deg C - 5 deg C, 20 min
7: 95 percent / EtMgBr / diethyl ether; benzene / 1 h / Heating
8: TFA / 23 h / Ambient temperature
9: BuLi / tetrahydrofuran; hexane / -10 °C
10: PPTS / dimethylformamide / 2 h / 80 °C
11: 95 percent / LiAlH4 / tetrahydrofuran / 18 h / Heating
12: 95 percent / MnO2 / diethyl ether / 15 h / Ambient temperature
With
pyridine; chromium(VI) oxide; manganese(IV) oxide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; dimethylsulfide borane complex; ethylmagnesium bromide; water; dihydrogen peroxide; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; trifluoroacetic acid;
pyridinium p-toluenesulfonate;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1002/hlca.19860690315