A novel synthetic method of the key intermediate 1-oxaspiro[4.5]dec-7-ene of U69593
U69593 is a common-used selective κ opioid receptor agonist.Herein,a novel synthetic route to the key intermediate 1-oxaspiro[4.5]dec-7-ene(1)of U69593 was reported.With 1,4-butanediol as the starting material,intermediate 1 was synthesized through eight steps of reactions,including mono-hydroxy protection,oxidation,amidation and olefin metathesis,with an overall yield up to 45.2％.The structure of intermediate 1 was confirmed by MS and NMR spectra.This method has the advantages of good reproducibility,low cost and easy availability of raw materials,mild reaction conditions,simple and safe operation,convenient scale-up synthesis and high application value.Furthermore,this is the first report on the synthesis of intermediate 1 via olefin metathesis reaction.
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