The synthesis and gastric antisecretory activities of the A4his, A4s6-trans, and 4, 5- acetylenic analogues of 15-deoxy-16-hydroxy-16-methyl prostaglandin El methyl ester are described. The key step in the preparation of these compounds involved the stereospecific conjugate addition of a cuprate reagent to the appropriate cyclopentenones. Although the trans and acetylenic derivatives were weak inhibitors of gastric acid secretion, the cis ...