反应详情

To a solution of (1R,10R,11S,16S)-3,5-dimethoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene (Compound No. 22) (187 mg, 0.5 mmol) in CH2Cl2 (20 mL) was added 3-chloroperoxybenzoic acid (77%, 112 mg, 0.5 mmol) portionwise at room temperature. The resulting mixture was stirred at room temperature for 2 h. CH2Cl2 (100 mL) was added and the mixture washed with saturated aqueous sodium bicarbonate (20 mL), dried (Na2SO4), and concentrated. Purification by chromatography on silica gel (Hexanes/EtOAc, 1:1) gave (1R,10R,11S,16S)-3,5-dimethoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-8-one (Compound No. 24) as separate diastereomers. (Diastereomer 1, white foam, 44 mg; Diastereomer 2, white solid, 290 mg).

1. washthe mixture washed with saturated aqueous sodium bicarbonate (20 mL)
2. dry with materialdried (Na2SO4)
3. concentrationconcentrated
4. customPurification by chromatography on silica gel (Hexanes/EtOAc, 1:1)