Dimethyl Sulfoxide → HCID 46862669, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of oxalyl chloride (68.4 mmoL) in dichloromethane (10 volumes) at −78° C. was added DMSO (114.0 mmoL). The solution was stirred at −78° C. for 30-60 minutes followed by drop-wise addition of (5Z)-benzyl 7-[(1R,2S,3R,5S)-3-benzyloxy-5-hydroxy-2-(hydroxymethyl)cyclopentyl]hept-5-enoate (16, R1 is phenyl, R2 and R3 are H and R7 is benzyl, 10 g, 22.8 mmoL) in dichloromethane (10 volumes). The reaction mixture was stirred at −78° C. for 30 minutes at which time triethylamine (105.9 mmoL) was charged. The mixture was stirred at −78 to −60° C. for 4-6 hours followed by quenching with saturated aqueous ammonium chloride (10 volumes). The mixture was warmed to 0° C. The layers were separated; the organic layer was washed with saturated aqueous sodium carbonate, dried over sodium sulfate, filtered through Celite® and concentrated to dryness. The residue was purified by column chromatography (50% ethyl acetate in heptanes) to yield (5Z)-benzyl 7-[(1R,2R,3R)-3-benzyloxy-2-formyl-5-oxocyclopentyl]hept-5-enoate (17, R1 is phenyl, R2 and R3 are H and R7 is benzyl) as an oil (9.8 g).

Provenance & Evidence