Multi-step reaction with 11 steps
1.1: 99 percent / 2,4,6-trichlorobenzoyl chloride; Et3N; 4-(dimethylamino)pyridine / toluene / 0.33 h / 20 °C
2.1: 96 percent / CF3COOH / CH2Cl2 / 4 h / 25 °C
3.1: 60 percent / PPh3; tBuCO2Na / Pd(OAc)2 / N,N-dimethyl-acetamide / 60 h / 110 °C
4.1: CH2Cl2 / 43 h / 0 °C
5.1: 97 percent / Cs2CO3 / dimethylformamide / 1.17 h / 0 - 20 °C
6.1: 100 percent / I2; PPh3; imidazole / CH2Cl2 / 0.33 h / 0 °C
7.1: 2.6-di-tert-butylpyridine / CH2Cl2 / 1 h / 20 °C
8.1: L-Selectride / 0.33 h / 0 °C
8.2: 96 percent / silica gel / 17 h / 20 °C
9.1: trimethylsilyl trifluoromethanesulfonate / toluene / 6 h / -15 °C
10.1: nBu4NF / tetrahydrofuran / 1 h / 0 °C
11.1: MnO2 / CH2Cl2 / 16 h / 20 °C
With
1H-imidazole; dmap; manganese(IV) oxide; 2,6-di-tert-butyl-pyridine; trimethylsilyl trifluoromethanesulfonate; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; iodine; L-Selectride; sodium pivalate; caesium carbonate; triethylamine; triphenylphosphine; trifluoroacetic acid;
palladium diacetate;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide; toluene;
1.1: Yamaguchi esterification;
DOI:10.1002/anie.200501210