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) (375 mg, 1.0 mmol) in CH2Cl2 (50 mL) was added BBr3 (1.0 M in CH2Cl2, 5.0 mL, 5.0 mmol) dropwise at 0° C., and the resulting mixture was stirred at room temperature overnight, then concentrated to dryness. Water (10 mL) was added at 0° C., followed by EtOAc (100 mL). The organic layer was separated, washed with brine (2×10 mL), dried (Na2SO4), and concentrated. Purification by chromatography on silica gel (Hexanes/EtOAc, 3:1) gave (1R,10R,11S,16S)-3-methoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-5-ol (Compound No. 25) (120 mg, 33%) as a white foam. 1H NMR (CDCl3): δ 6.15 (m, 2H), 4.46 (s, 1H), 3.78 (s, 3H), 3.25 (m, 1H), 2.90 (m, 1H), 2.76 (m, 1H), 1.84-1.32 (m, 6H), 1.30 (s, 3H), 1.29-1.00 (m, 4H), 0.95 (s, 3H), 0.94 (m, 1H), 0.85 (s, 3H), 0.85 (s, 3H). MS m/z 361 (C22H32O2S+H+).

1. concentrationconcentrated to dryness
2. additionWater (10 mL) was added at 0° C.
3. customThe organic layer was separated
4. washwashed with brine (2×10 mL)
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated
7. customPurification by chromatography on silica gel (Hexanes/EtOAc, 3:1)