Synthesis and gastric antisecretory properties of. alpha.-chain diene derivatives of misoprostol

PW Collins, AF Gasiecki, PH Jones…

Index: Collins, Paul W.; Gasiecki, Alan F.; Jones, Peter H.; Bauer, Raymond F.; Gullikson, Gary W.; et al. Journal of Medicinal Chemistry, 1986 , vol. 29, # 7 p. 1195 - 1201

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Citation Number: 7

Abstract

The synthesis and gastric antisecretory activity in dogs of seven a chain diene derivatives of misoprostol are described. The key intermediates in the preparation of these compounds were C-9 tert-butyldimethylsilyl enol ethers that were obtained by in situ silylation of cuprate enolates derived from a chain unsaturated cyclopentenones. Selenylation chemistry on these intermediates provided the C2-C3 trans dienes that, where possible, were also ...