Multi-step reaction with 9 steps
1.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.5 h / -75 °C
1.2: 42 percent / tetrahydrofuran; hexane / 1 h / -75 °C
2.1: 93 percent / N,N-diisopropylethylamine / CH2Cl2 / 16 h / 20 °C
3.1: LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C
4.1: 7.51 g / pyridine / 17 h / 20 °C
5.1: 91 percent / formic acid / diethyl ether / 1 h / -5 °C
6.1: NaOH / H2O; ethanol / 20 h / 20 °C
7.1: NaIO4 / 2-methyl-propan-2-ol; H2O / 1.5 h / 20 °C
7.2: 1.31 g / Ag2CO3/Celite / toluene / 1 h / Heating
8.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.5 h / -75 °C
8.2: tetrahydrofuran; hexane / 3.5 h / -75 - 0 °C
8.3: 58 percent / methyl iodide / tetrahydrofuran; hexane / 56 h / 20 °C
9.1: 69 percent / trimethylsilylbromide / CH2Cl2 / 1 h / -20 °C
With
pyridine; sodium hydroxide; sodium periodate; lithium aluminium tetrahydride; formic acid; trimethylsilyl bromide; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; tert-butyl alcohol;
DOI:10.1271/bbb.64.2209