Boron tribromide → (1R,10R,11S,16S)-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-5-ol

Participants

Reaction Steps

To a solution of (1R,10R,11S,16S)-5-methoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene (51) (0.25 g, 0.73 mmol) in CH2Cl2 (10 mL), cooled to 0° C., a solution of BBr3 (1.0 M in CH2Cl2, 2.90 mL, 2.90 mmol) was added and the resulting mixture was stirred at room temperature for 24 h. The reaction was quenched with MeOH (3×10 mL) and concentrated to dryness. Purification by column chromatography on silica gel (Hexanes/EtOAc, 10:1) gave (1R,10R,11S,16S)-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-trien-5-ol (Compound No. 53) (0.22 g, 92%) as a white solid. 1H NMR (CDCl3): δ 7.14 (d, 1H), 6.49 (m, 2H), 4.45 (br s, 1H), 2.95 (q, 2H), 2.40 (m, 1H), 1.84-1.35 (m, 9H), 1.20 (s, 3H), 1.18-0.98 (m, 2H), 0.95 (s, 3H), 0.88 (m, 3H), 0.85 (s, 3H).

Provenance & Evidence