New concise total synthesis of (+)-lentiginosine and some structural analogues

J Org Chem. 2005 Aug 5;70(16):6552-5. doi: 10.1021/jo0509408.

Abstract

An efficient and concise total synthesis of (+)-lentiginosine (1) starting from an L-tartaric acid-derived nitrone using organometallic addition, indium-catalyzed reduction, and ring-closing metathesis reaction as the key steps is reported. Structural analogues of (+)-1 have been also synthesized, and their inhibitory activity toward 22 commercially available glycosidases has been evaluated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry*
  • Alkaloids / pharmacology
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Glycoside Hydrolases / antagonists & inhibitors
  • Glycoside Hydrolases / metabolism
  • Molecular Structure
  • Nitrogen Oxides / chemistry
  • Tartrates / chemistry

Substances

  • Alkaloids
  • Enzyme Inhibitors
  • Nitrogen Oxides
  • Tartrates
  • nitrones
  • lentiginosine
  • Glycoside Hydrolases
  • tartaric acid