Abstract
Two configurationally stable carbon-based analogues of pyochelin have been prepared from Boc-pyroglutamic acid-tert-butyl ester in 11 and 13 steps. Introduction of the amino group was achieved by a highly diastereoselective electrophilic azidation reaction to afford novel bis-alpha-amino acid proline derivatives.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Azides / chemistry*
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Crystallography, X-Ray
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Models, Molecular
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Molecular Conformation
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Phenols / chemical synthesis*
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Phenols / chemistry
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Proline / analogs & derivatives*
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Proline / chemistry*
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Stereoisomerism
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Thiazoles / chemical synthesis*
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Thiazoles / chemistry
Substances
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5-(ethoxycarbonyl)methylproline
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Azides
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Phenols
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Thiazoles
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pyochelin
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Proline