Abstract
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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Amino Acids / chemical synthesis*
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Amino Acids / chemistry
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Optical Phenomena*
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Oxidation-Reduction
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Pyrroles / chemistry*
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Pyrrolidinones / chemical synthesis*
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Pyrrolidinones / chemistry
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Pyrrolidonecarboxylic Acid / chemistry*
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Silanes / chemistry*
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Stereoisomerism
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Substrate Specificity
Substances
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Amino Acids
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N-triisopropylsilylpyrrole
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Pyrroles
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Pyrrolidinones
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Silanes
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penmacric acid
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Pyrrolidonecarboxylic Acid