Synthesis of 2-[4'-(ethylcarbamoyl)phenyl]-N-acetylglycine, the proposed structure for giganticine.
A compound (1) with the structure proposed for giganticine, an antifeedant principle isolated from the root bark of Caloropis gigantea, has been successfully synthesized by two independent methods. Comparison of physical properties and spectroscopic data of 1 with giganticine revealed that they are different compounds. All available evidence suggests that the proposed structure of giganticine is incorrect.
Suparpprom
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Organic Synthesis Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Phayathai Road, Patumwan, Bangkok 10330, Thailand.
Vilaivan
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D000818:Animals; D005247:Feeding Behavior / Q000187:drug effects; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification*; D006110:Grasshoppers / Q000187:drug effects; D007194:India; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry / Q000379:methods; D015394:Molecular Structure; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D013055:Spectrophotometry, Infrared
C436809:2-(4'-(ethylcarbamoyl)phenyl)-N-acetylglycine; C436810:giganticine; D005998:Glycine