Multi-step reaction with 11 steps
1.1: nBu2BOTf; N,N-diisopropylethylamine / CH2Cl2 / 0.5 h / -5 °C
1.2: 3.98 g / CH2Cl2 / 16 h / -78 °C
2.1: 2,6-lutidine / CH2Cl2 / 1 h / Heating
3.1: lithium hydroxide monohydrate; hydrogen peroxide / tetrahydrofuran; H2O / 36 h / 20 °C
4.1: 1,1'-carbonyldiimidazole / CH2Cl2 / 0.5 h / 0 °C
4.2: 2.07 g / CH2Cl2 / 16 h / 20 °C
5.1: 78 percent / tetrahydrofuran; diethyl ether / 1.25 h / -20 - 0 °C
6.1: 1.16 g / dimethylaluminum chloride; tributyltin hydride / CH2Cl2; hexane / 1 h / -90 °C
7.1: 85 percent / proton sponge(R) / CHCl3 / 16 h / Heating
8.1: 98 percent / hydrogen / palladium hydroxide on carbon / ethanol / 3 h / 20 °C / atmospheric pressure
9.1: 91 percent / tributylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 °C
10.1: 86 percent / hydrogen peroxide; Mo7O24(NH4)6*4H2O / ethanol; H2O / 16 h / 20 °C
11.1: 75 percent Turnov. / sodium hexamethyldisilazide / 1,2-dimethoxy-ethane; hexamethylphosphoric acid triamide; tetrahydrofuran / 2 h / -78 °C
With
2,6-dimethylpyridine; lithium hydroxide; ammonium molybdate tetrahydrate; tributylphosphine; di-isopropyl azodicarboxylate; di-n-butylboryl trifluoromethanesulfonate; hydrogen; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; dimethylaluminum chloride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole;
palladium dihydroxide;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; diethyl ether; ethanol; hexane; dichloromethane; chloroform; water;
9.1: Mitsunobu reaction / 11.1: Julia-Kocienski olefination;
DOI:10.1021/ol060669w