Multi-step reaction with 10 steps
1.1: 100 percent / potassium bicarbonate / dimethylformamide / 10 h / 20 °C
2.1: DIBAL-H / toluene; CH2Cl2 / 2 h / -78 °C
3.1: toluene; CH2Cl2; tetrahydrofuran / 6 h / -78 - 0 °C
4.1: aq. HCl; anisole / dioxane / 2 h / 20 °C
5.1: 3.2 g / Et3N; pyridine / CHCl3 / 12 h / 20 °C
6.1: 93 percent / PPh3; diethyl azodicarboxylate / toluene; tetrahydrofuran / 0.5 h / 20 °C
7.1: O3 / CH2Cl2 / -78 °C
7.2: Me2S / CH2Cl2 / 0.5 h
8.1: DIPEA; LiCl / acetonitrile / 0.33 h / 0 °C
8.2: 1.0 g / acetonitrile / 8 h / 0 °C
9.1: CHCl3 / 0.33 h / 20 °C
10.1: CuCN / tetrahydrofuran / 0.25 h / 0 °C
10.2: BF3*Et2O / tetrahydrofuran / 0.25 h / -78 °C
10.3: 408 mg / tetrahydrofuran / 1 h / -78 °C
With
pyridine; hydrogenchloride; diisobutylaluminium hydride; potassium hydrogencarbonate; ozone; methoxybenzene; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; diethylazodicarboxylate;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; acetonitrile;
6.1: Mitsunobu reaction;
DOI:10.1021/jm049429h