Synthesis of 2-[4'-(ethylcarbamoyl)phenyl]-N-acetylglycine, the proposed structure for giganticine

C Suparpprom; T Vilaivan

doi:10.1021/np010046l

Synthesis of 2-[4'-(ethylcarbamoyl)phenyl]-N-acetylglycine, the proposed structure for giganticine

J Nat Prod. 2001 Aug;64(8):1114-6. doi: 10.1021/np010046l.

Authors

C Suparpprom¹, T Vilaivan

Affiliation

¹ Organic Synthesis Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Phayathai Road, Patumwan, Bangkok 10330, Thailand.

PMID: 11520243
DOI: 10.1021/np010046l

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Feeding Behavior / drug effects
Glycine / analogs & derivatives
Glycine / chemistry
Glycine / isolation & purification*
Grasshoppers / drug effects
India
Magnetic Resonance Spectroscopy
Mass Spectrometry / methods
Molecular Structure
Plant Roots / chemistry
Plants, Medicinal / chemistry*
Spectrophotometry, Infrared

Substances

2-(4'-(ethylcarbamoyl)phenyl)-N-acetylglycine
giganticine
Glycine