dysiherbaine and 4-hydroxy-4-(indol-3-ylmethyl)glutamic-acid

dysiherbaine has been researched along with 4-hydroxy-4-(indol-3-ylmethyl)glutamic-acid* in 1 studies

Other Studies

1 other study(ies) available for dysiherbaine and 4-hydroxy-4-(indol-3-ylmethyl)glutamic-acid

Article	Year
Stereoselective syntheses of 4-hydroxy 4-substituted glutamic acids. The Journal of organic chemistry, 2005, Jun-10, Volume: 70, Issue:12 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. Topics: Alanine; Bridged Bicyclo Compounds, Heterocyclic; Catalysis; Cyclization; Glutamic Acid; Indicators and Reagents; Indoles; Molecular Structure; Stereoisomerism	2005

Article

Year

Stereoselective syntheses of 4-hydroxy 4-substituted glutamic acids.

The Journal of organic chemistry, 2005, Jun-10, Volume: 70, Issue:12

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.

Topics: Alanine; Bridged Bicyclo Compounds, Heterocyclic; Catalysis; Cyclization; Glutamic Acid; Indicators and Reagents; Indoles; Molecular Structure; Stereoisomerism

2005