AI Article Synopsis
- The study focuses on synthesizing the 4-hydroxy 4-substituted glutamic acid structure found in important natural products like monatin, lycoperdic acid, and dysiherbaine.
- Researchers explored cycloadditions between nitrone and substituted propen-1-ols or acrylates to create various cycloadducts.
- The method resulted in successful syntheses of monatin, its derivative, and lycoperdic acid, and also enabled the creation of a C4-epimer of monatin.
Article Abstract
The 4-hydroxy 4-substituted glutamic acid moiety is a common substructure of biologically important natural products such as monatin [(2S,4S)-2], lycoperdic acid (3), and dysiherbaine (4). To develop methodology for syntheses of these natural products, cycloadditions of nitrone 5 with 2-substituted 2-propen-1-ols 6 and 2-substituted acrylates 8 were investigated. Reactions of nitrone 5 with alcohols 6 in the presence of MgBr2OEt2 gave cycloadducts 7 in a highly stereoselective manner, whereas noncatalyzed reactions of 5 with acrylates 8 afforded adducts 9. Using the former reaction, syntheses of monatin [(2S,4S)-2], monatin derivative 18, and lycoperdic acid (3) were accomplished. The C4-epimer of monatin [(2S,4R)-2)] was also synthesized by employing the latter cycloaddition.
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| http://dx.doi.org/10.1021/jo040296h | DOI Listing |
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