A monocyclic neodysiherbaine analog: Synthesis and evaluation

Bioorg Med Chem Lett. 2016 Nov 1;26(21):5164-5167. doi: 10.1016/j.bmcl.2016.09.074. Epub 2016 Sep 30.


Monocyclic analog of neuroexcitatory neodysiherbaine has been designed and stereoselectively synthesized in 0.40% yield over total 24 steps starting from d-ribose, by employing domino aldol-Cannizzaro reaction and stereoselective aldol reaction for construction of two quaternary carbon stereogenic centers at C4 and C6 positions, respectively. The hyperactivity of neodysiherbaine in mice was found to deteriorate in the novel analog, upon intracerebroventricular injection.

Keywords: Aldol reaction; Dihydroxylation; Domino reaction; Excitatory amino acid; Natural product analog; Neodysiherbaine; Neuroactivity; Stereoselective synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alanine / analogs & derivatives*
  • Alanine / chemical synthesis
  • Alanine / chemistry
  • Alanine / pharmacology
  • Animals
  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry
  • Bridged Bicyclo Compounds, Heterocyclic / pharmacology
  • Dose-Response Relationship, Drug
  • Drug Evaluation, Preclinical
  • Magnetic Resonance Spectroscopy
  • Mice
  • Structure-Activity Relationship


  • Bridged Bicyclo Compounds, Heterocyclic
  • neodysiherbaine A
  • Alanine