11, 12-Secoprostaglandins. 6. Interphenylene analogs of acylhydroxyalkanoic acids and related compounds as renal vasodilators

…, EJ Cragoe Jr, EH Blaine, LS Watson…

Index: Bicking, John B.; Robb, Charles M.; Cragoe, Edward J.; Blaine, Edward H.; Watson, L. Sherman; Dunlay, Mary C. Journal of Medicinal Chemistry, 1983 , vol. 26, # 3 p. 335 - 341

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Citation Number: 9

Abstract

22 resulting dicarboxylic esters 18a-e were alkylated with 1-chloro-4-acetoxynonane. Esters 19a-e so produced were subjected to acid-catalyzed elimination-decarboxylation and saponification to yield 5-9. A route involving acid-catalyzed cleavage of the tert- butoxycarbonyl group is precluded for the synthesis of 11 in which an acylated propargylic alcohol is an intermediate and, likewise, undergoes a facile acid-catalyzed elimination. ...