Multi-step reaction with 8 steps
1: 1.) O3, 2.) NaBH3CN / 1.) CH2Cl2, -78 deg C, 3 h, 2.) i-PrOH, 48 h
2: 72 percent / 48 h / 135 °C
3: HMDS / pentane; CH2Cl2 / 6 h / -20 °C
4: Ph2Se2 / tetrahydrofuran / 3 h / -35 - 20 °C
5: 1.) O3, i-Pr2NEt / 1.) -78 deg C, CH2Cl2, 2.) room temperature, 15 min
6: methanol / 3 h / Heating
7: K2CO3 / butan-2-one / 5 h / Heating
8: BF3*Et2O / CH2Cl2 / Heating
With
diphenyl diselenide; boron trifluoride diethyl etherate; sodium cyanoborohydride; potassium carbonate; ozone; N-ethyl-N,N-diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane;
In
tetrahydrofuran; methanol; dichloromethane; butanone; pentane;
DOI:10.1021/ja970347a