Synthesis of a NO-releasing prodrug of rofecoxib

…, CJ Cowden, DA Conlon, B Pipik, G Zhou…

Index: Engelhardt, F. Conrad; Shi, Yao-Jun; Cowden, Cameron J.; Conlon, David A.; Pipik, Brenda; Zhou, George; McNamara, James M.; Dolling, Ulf-H. Journal of Organic Chemistry, 2006 , vol. 71, # 2 p. 480 - 491

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Citation Number: 32

Abstract

A newly developed synthesis of a NO-releasing prodrug of rofecoxib is described. The highly productive process consists of five chemical steps and produces prodrug 1 in an overall 64% yield from commercially available 3-phenyl-2-propyn-1-ol (4). The synthesis is highlighted by the carbometalation reaction of propargyl alcohol 4 to generate the tetrasubstituted olefin core, sulfone acid 2. Additionally, two alternate end-game strategies ...