Multi-step reaction with 14 steps
1.1: Ba(OH)2*8H2O / dioxane; H2O / 60 °C
1.2: 88 percent / CSA / CH2Cl2; methanol / 20 °C
2.1: 2,4,6-Cl3C6H2COCl; Et3N / tetrahydrofuran / 20 °C
2.2: 71 percent / DMAP / benzene / 80 °C
3.1: 6.39 g / potassium hexamethyldisilazide; hexamethylphosphoric triamide / tetrahydrofuran; toluene / 0.67 h / -78 °C
4.1: 76 percent / triethylamine / tetrakis(triphenylphosphine)palladium(0) / dimethylformamide / 15 h / 50 °C
5.1: AD mix-α; methanesulfonamide / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 48 h / 20 °C
6.1: 79 percent / 10-camphorsulfonic acid / CH2Cl2 / 1 h / 20 °C
7.1: DIBALH / CH2Cl2; toluene / 0.5 h / -78 °C
8.1: 2,6-lutidine / CH2Cl2 / 0 - 20 °C
9.1: dimethyldioxirane / CH2Cl2; acetone / 1 h / -20 °C
10.1: 75 percent / triethylsilane; BH3*THF / CH2Cl2; tetrahydrofuran / 0.33 h / 0 °C
11.1: 97 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.25 h / 20 °C
12.1: 98 percent / potassium tert-butoxide / tetrahydrofuran / 0.42 h / 20 °C
13.1: ethanethiol; zinc triflate / CH2Cl2 / 26 h / 20 °C
14.1: 78 percent / CH2Cl2 / 0.33 h / 20 °C
With
2,6-dimethylpyridine; triethylsilane; N,N,N,N,N,N-hexamethylphosphoric triamide; barium dihydroxide; AD-mix-α; borane-THF; methanesulfonamide; 2,4,6-trichlorobenzoyl chloride; (1S)-10-camphorsulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; potassium hexamethylsilazane; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; triethylamine; ethanethiol;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;
DOI:10.1021/ol026306n