Synthesis and fucosidase inhibitory study of unnatural pyrrolidine alkaloid 4-epi-(+)-codonopsinine

J Org Chem. 2011 May 20;76(10):4094-8. doi: 10.1021/jo200176u. Epub 2011 Apr 28.

Abstract

The total synthesis of enantiopure 4-epi-(+)-codonopsinine was achieved in 10 steps starting from D-ribose as a chiral building block. The key step involved a highly stereoselective nucleophilic addition of a Grignard reagent to a protected ribosylamine. Synthesis of the N-desmethyl derivative and its p-tolyl analogue was also accomplished, and the compounds were assayed against α-fucosidase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cattle
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Pyrrolidines / chemical synthesis*
  • Pyrrolidines / chemistry
  • Pyrrolidines / pharmacology*
  • Stereoisomerism
  • Substrate Specificity
  • alpha-L-Fucosidase / antagonists & inhibitors*

Substances

  • Enzyme Inhibitors
  • Pyrrolidines
  • codonopsinine
  • alpha-L-Fucosidase