Journal of Medicinal Chemistry 1987-11-01

Synthesis and gastrointestinal pharmacology of the 4-fluoro analogue of enisoprost.

P W Collins, S W Kramer, G W Gullikson

Index: J. Med. Chem. 30 , 1952, (1987)

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Abstract

A 4-fluoro analogue of enisoprost was prepared and evaluated for gastric antisecretory and mucosal protective activity in animals. The synthesis centered upon cuprate chemistry but also involved a Wittig reaction to produce a cis fluoro olefinic moiety, a furan rearrangement/isomerization reaction to provide the necessary hydroxycyclopentenone, and a two-carbon-homologation procedure. The fluoro analogue was much less potent as a gastric antisecretory and mucosal protective agent than enisoprost.