Hemisynthesis of coumarin derivatives from Ammodaucus leucotrichus oil extract: organobase-catalyzed reaction, analytical study by diffusion-ordered spectroscopy NMR and differential scanning calorimetry

Nat Prod Res. 2022 May;36(9):2284-2291. doi: 10.1080/14786419.2020.1828408. Epub 2020 Nov 13.

Abstract

This paper presents an in-depth chemical and analytical study of a natural substance extracted from Ammodaucus leucotrichus Coss. & Dur and its derivatives after hemisynthesis. The analysis was performed using Diffusion-Ordered Spectroscopy (NMR DOSY) and Differential Scanning Calorimetry (DSC) as general methods. The results show an interesting chemical reactivity towards coumarin-derived bisnucleophiles (4-hydroxycoumarin and triacetic acid lactone), and products obtained by hemisynthesis of pyrano[4,3-b]pyrane derivatives following Knoevenagel condensation and Michael's addition on this natural substance with the use of 4-pyrolidinopyridine organobase as catalyst.

Keywords: Ammodaucus leucotrichus; Analytical study (NMR DOSY; DSC); Hemisynthesis; coumarin.

MeSH terms

  • Apiaceae* / chemistry
  • Calorimetry, Differential Scanning
  • Catalysis
  • Coumarins
  • Magnetic Resonance Spectroscopy / methods
  • Plant Extracts / chemistry

Substances

  • Coumarins
  • Plant Extracts