Synthesis and kinetic studies of a simple prostacyclin model

…, M Jansson, Y Chiang, AJ Kresge, Y Yin

Index: Bergman, Nils-Ake; Jansson, Marie; Chiang, Yvonne; Kresge, A. Jerry; Yin, Ya Journal of Organic Chemistry, 1987 , vol. 52, # 20 p. 4449 - 4453

Full Text: HTML

Citation Number: 12

Abstract

A simple prostacyclin model,(2)-6, 9-epoxynon-5-enoic acid, has been synthesized, and the rate of hydrolysis of the vinyl ether functional group of it and ita methyl ester has been measured by monitoring UV spectral changes over the pH range 1-8 at 25.0 f 0.1" C and total ionic strength 0.1 M. The measurements show that (Z)-6, 9-epoxynon-5-enoic acid is 82 times more reactive than its methyl ester at high pH when the carboxylic acid group is in ...