反应详情

To a solution of (1R,10R,11S,16S)-3-methoxy-1,5,11,15,15-pentamethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene (Compound No. 14) (1.16 g, 3.23 mmol) in CH2Cl2 (100 mL) was added BBr3 (1.0 M in CH2Cl2, 9.70 mL, 9.70 mmol) dropwise at 0° C., and the resulting mixture stirred at room temperature overnight, then concentrated to dryness. Water (20 mL) was added at 0° C., followed by EtOAc (100 mL). The organic layer was separated, washed with brine (2×20 mL), dried (Na2SO4), and concentrated. Purification by chromatography on silica gel (Hexanes/EtOAc, 9:1) gave (1R,10R,11S,16S)-1,5,11,15,15-pentamethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-3-ol (Compound No. 15) (0.88 g, 79%) as a white solid. 1H NMR (CDCl3): δ 6.50 (s, 1H), 6.15 (s, 1H), 4.60 (s, 1H), 3.38 (m, 1H), 2.90 (m, 1H), 2.78 (m, 1H), 2.18 (s, 3H), 1.84-1.42 (m, 9H), 1.40 (s, 3H), 1.20-1.00 (m, 2H), 0.98 (s, 3H), 0.89 (s, 3H), 0.89 (s, 3H). MS m/z 343 (C22H32OS−H+).

1. concentrationconcentrated to dryness
2. additionWater (20 mL) was added at 0° C.
3. customThe organic layer was separated
4. washwashed with brine (2×20 mL)
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated
7. customPurification by chromatography on silica gel (Hexanes/EtOAc, 9:1)