Multi-step reaction with 10 steps
1.1: dimethyldioxirane / CH2Cl2 / 0.5 h / 0 °C
2.1: 2.52 g / CH2Cl2; tetrahydrofuran / 9 h / -60 - 20 °C
3.1: 77 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 20 °C
4.1: ozone / CH2Cl2 / -78 °C
4.2: triphenylphosphine / CH2Cl2 / 2 h / 20 °C
5.1: 0.396 g / titanium(IV) isopropoxide / tetrahydrofuran / 4 h / 20 °C
6.1: CH2Cl2; diethyl ether / 1 h / -78 °C
7.1: 68 percent / hydrochloric acid / methanol; H2O / 1 h / 20 °C
8.1: 0.270 g / triethylamine / CH2Cl2 / 8 h / 43 °C
9.1: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C
10.1: 97 percent / N,N-diisopropylethylamine / CH2Cl2 / 8 h / 40 °C
With
2,6-dimethylpyridine; titanium(IV) isopropylate; hydrogenchloride; tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; ozone; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;
DOI:10.1021/ol034273l