Synthesis of a Prostaglandin EP4 Receptor Antagonist

D. Gauvreau; S. J. Dolman; G. Hughes; P. D. O’Shea; I. W. Davies

doi:10.1055/s-0030-1257875

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Synfacts 2010(9): 0981-0981
DOI: 10.1055/s-0030-1257875

Synthesis of Natural Products and Potential Drugs

Synthesis of a Prostaglandin EP4 Receptor Antagonist

Contributor(s): Philip Kocienski
D. Gauvreau*, S. J. Dolman, G. Hughes, P. D. O’Shea, I. W. Davies
Merck Frosst Centre for Therapeutic Research, Kirkland, Canada

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Publication History

Publication Date:
23 August 2010 (online)

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Significance

EP4 Receptor antagonists are candidates for the treatment of inflammatory disorders associated with arachidonic acid metabolism. Noteworthy steps in the synthesis shown were (1) a large-scale Kulinkovich cyclopropanation (A → B), (2) an FeCl₃-catalyzed Friedel-Crafts benzylation of 2,5-dimethylthiophene (E) using 4-trifluoromethylbenzyl alcohol (D) as the electrophile and (3) an FeCl₃-catalyzed Friedel-Crafts acylation of thiophene F using isocyanate C as the electrophile.