Tetrahedron

Synthesis of 2-(4-carboxybutenyl)-and 2-(4-carboxybutynyl)-cyclopentene-1-carboxamides

A Beauchard, VA Phillips, MD Lloyd, MD Threadgill

Index: Beauchard, Anne; Phillips, Victoria A.; Lloyd, Matthew D.; Threadgill, Michael D. Tetrahedron, 2009 , vol. 65, # 39 p. 8176 - 8184

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Citation Number: 8

Abstract

Syntheses of 2-(4-carboxybut-1-enyl/4-carboxypent-1-ynyl) cyclopentene-1-carboxamides, compounds designed to mimic the phosphoSer–Pro dipeptide motif (the recognition sequence for the prolyl cis–trans isomerase Pin1), have been developed. Stille, Sonogashira and Suzuki couplings were envisaged to join the pentynoic and pentenoic acid side chains to the 2-position of cyclopentene-1-carboxylate esters. The ring-and side- ...

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