From N-triisopropylsilylpyrrole to an optically active C-4 substituted pyroglutamic acid: total synthesis of penmacric acid

The stereoselective synthesis of penmacric acid, an optically active C-4 substituted pyroglutamic acid, has been efficiently achieved through an unusual 11-step sequence starting from simple N-triisopropylsilylpyrrole. The key-steps are the initial addition of the pyrrole nucleus onto a chiral nitro...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 7; no. 21
Main Authors Berini, Christophe, Pelloux-Léon, Nadia, Minassian, Frédéric, Denis, Jean-Noël
Format Journal Article
LanguageEnglish
Published Royal Society of Chemistry 2009
Subjects
Chemical Sciences
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Summary:The stereoselective synthesis of penmacric acid, an optically active C-4 substituted pyroglutamic acid, has been efficiently achieved through an unusual 11-step sequence starting from simple N-triisopropylsilylpyrrole. The key-steps are the initial addition of the pyrrole nucleus onto a chiral nitrone and the obtention of the pyroglutamic acid moiety by reductive hydrogenation of the pyrrole followed by oxidation of the corresponding pyrrolidine into pyrrolidinone.
ISSN:1477-0520
1477-0539
DOI:10.1039/b911217k