Multi-step reaction with 15 steps
1.1: trimethylaluminum / tetrahydrofuran; toluene / 0 - 20 °C
1.2: 100 percent / tetrahydrofuran; toluene / 1 h / 0 °C
2.1: 100 percent / imidazole / dimethylformamide / 0.75 h / 20 °C
3.1: 91 percent / DIBAL / tetrahydrofuran; hexane / 2 h / -78 °C
4.1: 40 percent / lithium diisopropylamide / tetrahydrofuran / 0.75 h / -78 °C
5.1: 95 percent / imidazole / dimethylformamide / 1.5 h / 20 °C
6.1: 93 percent / DIBAL / CH2Cl2; hexane / 2 h / -23 °C
7.1: 84 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 1 h / -78 °C
8.1: 86 percent / NaH / 1,2-dimethoxy-ethane / 1 h / -10 °C
9.1: 98 percent / HF*pyridine; pyridine / tetrahydrofuran / 0.67 h / 20 °C
10.1: 60 percent / MnO2 / CH2Cl2 / 12 h / 20 °C
11.1: 89 percent / imidazole / dimethylformamide / 2 h / 20 °C
12.1: CeCl3*7H2O; NaBH4 / ethanol / -78 - -23 °C
13.1: HF*pyridine; pyridine / tetrahydrofuran / 0.5 h / 20 °C
14.1: DIBAL / CH2Cl2; hexane / 1.5 h / -23 °C
15.1: 1.2 mg / pyridine / 12 h / 20 °C
With
pyridine; 1H-imidazole; manganese(IV) oxide; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; trimethylaluminum; sodium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide;
In
tetrahydrofuran; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
7.1: Swern oxidation / 8.1: Horner-Emmons reaction;
DOI:10.1016/j.tet.2004.06.125