Isolation and synthesis of an alpha-malamic acid derivative from Justicia ghiesbreghtiana.
A polar extract of leaves of Justicia ghiesbreghtiana yielded N-(2-hydroxy-4,5-dimethoxyphenyl)-(S)-alpha-malamic acid, 1. Incomplete spectral analysis yielded a hypothetical structure, which was then proven by total synthesis. Coupling of the trifluoroacetate of malic anhydride (trifluoroacetoxysuccinic anhydride) with an arylamine provided the key to regiospecific preparation of the alpha- rather than beta-malamic acids.
Ismail
L D
LD
Department of Pharmacognosy, Al-Azhar University, Nasr City, Cairo, Egypt.
Lorenz
P
P
Stermitz
F R
FR
D000814:Aniline Compounds / Q000737:chemistry* / Q000302:isolation & purification; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D002264:Carboxylic Acids / Q000737:chemistry* / Q000302:isolation & purification; D005658:Fungi / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D018515:Plant Leaves / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry*; D014920:Wine / Q000032:analysis
D000814:Aniline Compounds; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D002264:Carboxylic Acids; C115551:N-(2-hydroxy-4,5-dimethoxyphenyl)malamic acid