Tetrahedron p. 6001 - 6018 (1999)
Update date:2022-08-04
Topics:
Zhao, Dalian
Feng, Xu
Chen, Cheng-yi
Tillyer, Rich D.
Grabowski, Edward J. J.
Reider, Paul J.
Black, Cameron
Quimet, Nathalie
Prasit, Peppi
2-(3',5'-Difluorophenyl)-3-(4'-methylsulfonylphenyl)cyclopent-2-enone (1) displays high selectivity and potency against COX-2. Three efficient syntheses of this diarylcyclopentenone are described. The first approach employs a Suzuki coupling reaction as the key step while the second synthesis features an intramolecular Friedel-Crafts acylation. The third, and preferred route to this compound involves a sequential malonate alkylation and acylation and ring-closure sequence.
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