Synthesis of the Angiotensin Converting Enzyme Inhibitor (−)-A58365A via an Cycloaddition Reaction

The angiotensin converting enzyme inhibitor (−)-A58365A (1) was synthesized by a process based on the [3 + 2]-cycloaddition reaction of a phenylsulfonyl-substituted intermediate. The starting material for this process was prepared from l-pyroglutamic acid and involved using a diazo-phenylsulfonyl-su...

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Bibliographic Details
Published inOrganic letters Vol. 1; no. 1; pp. 83 - 86
Main Authors Straub, Christopher S, Padwa, Albert
Format Journal Article
LanguageEnglish
Published American Chemical Society 15.07.1999
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Summary:The angiotensin converting enzyme inhibitor (−)-A58365A (1) was synthesized by a process based on the [3 + 2]-cycloaddition reaction of a phenylsulfonyl-substituted intermediate. The starting material for this process was prepared from l-pyroglutamic acid and involved using a diazo-phenylsulfonyl-substituted pyrrolidine imide. Treatment of the diazoimide with Rh2(OAc)4 in the presence of methyl vinyl ketone afforded a 3-hydroxy-2-pyridone derivative which was subsequently converted to the ACE inhibitor in six additional steps.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol9905497