Endo-1,4a,8,8a-tetrahydro-1,4-ethanonaphthalene-5,8-dione → 1,4,4a,5,8,8a-Hexahydro-1,4-ethanonaphthalene-5,8-diol
반응식
[CH:1]12[CH2:12][CH2:11][CH:8]([CH:9]=[CH:10]1)[CH:7]1[CH:2]2[C:3](=[O:14])[CH:4]=[CH:5][C:6]1=[O:13].[BH4-].[Na+]>CO>[CH:8]12[CH2:11][CH2:12][CH:1]([CH:10]=[CH:9]1)[CH:2]1[CH:7]2[CH:6]([OH:13])[CH:5]=[CH:4][CH:3]1[OH:14]참가 물질
4
실험 절차
To a solution of 25.6 g of tricyclo[6.2.2.02,7]dodeca-4,9-diene-3,6-dione in 600 mL of MeOH were added 58.0 g of CeCl3 7H2O. Then, 5.7 g of NaBH4 were portionwise added at 0° C. and the mixture was stirred for 1 h at the same temperature. After evaporation of the solvent the residue was redissolved in EtOAc, it was washed with H2O, dried over MgSO4 and concentrated in vacuo. The crude was again redissolved in EtOAc and triturated with Hept to obtain 27.9 g of the desired compound as mixture of stereoisomers as brownish solid.