Synthesis and gastrointestinal pharmacology of a 3E, 5Z diene analog of misoprostol

PW Collins, SW Kramer, AF Gasiecki…

Index: Collins, Paul W.; Kramer, Steven W.; Gasiecki, Alan F.; Weier, Richard M.; Jones, Peter H.; et al. Journal of Medicinal Chemistry, 1987 , vol. 30, # 1 p. 193 - 197

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Citation Number: 21

Abstract

A stereospecific synthesis and the gastric antisecretory and diarrheal activity of a 3E, 5Z diene analogue of misoprostol are described. The key intermediate in the synthesis was an CY chain truncated acetylene that was obtained by a cuprate/enolate capture procedure on the corresponding cyclopentenone. Palladium-catalyzed coupling of the acetylene with methyl 4-iodo-3 (E)-butenoate provided the conjugated enyne. Although selective ...