Dichloromethane → HCID 86654186, compound

Participants

Reaction Steps

To a solution of (1R,10S,11S,16S)-3,5-dimethoxy-11,15,15-trimethyl-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-8,8-dione (23) (7.6 g, 18.7 mmol) in CH2Cl2 (250 mL) BBr3 (1 M in CH2Cl2 18.7 mL, 18.7 mmol) was added dropwise at room temperature under N2. The mixture was stirred at room temperature for 18 h. Additional BBr3 (1 M in CH2Cl2 18.7 mL, 18.7 mmol) was added to the reaction and stirring continued for another 6 h. The mixture was poured onto crushed ice and the organic layer was separated and concentrated to dryness. The residue was purified by flash chromatography on silica gel (Hexanes/EtOAc, 3:1) to yield (1R,10S,11S,16S)-5-hydroxy-3-methoxy-11,15,15-trimethyl-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-8,8-dione (57) (4.2 g, 57%) as a pale brown solid.

Provenance & Evidence