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A general carbometalation, three component coupling strategy for the synthesis of alpha,beta-unsaturated gamma-sultines including thio-rofecoxib, a selective COX-2 inhibitor.

Smil DV, Souza FE, Fallis AG

Methyl Gene Inc., 7220 Frederick Banting, Montreal, Québec, Canada H4S 2A1.

Magnesium mediated carbometalation (Grignard addition) to appropriate propargyl alcohols to synthesize a cross-section of variably substituted alpha,beta-unsaturated gamma-sultines is described. Thio-rofecoxib, a selective COX-2 inhibitor (12), is synthesized by this method and its IC(50), microM COX-1 and COX-2 inhibition, and whole blood stability values reported.

Published 5 April 2005 in Bioorg Med Chem Lett, 15(8): 2057-60.
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