title: Synthesis and fucosidase inhibitory study of unnatural pyrrolidine alkaloid 4-epi-(+)-codonopsinine.
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.
authors.affiliation: Institut de Chimie Moléculaire de Reims, UFR Sciences, CNRS, BP 1039, 51687 Reims Cedex 2, France.
authors.forename: Alexis
authors.initials: A
authors.lastname: Kotland
authors.forename: Fabien
authors.initials: F
authors.lastname: Accadbled
authors.forename: Koen
authors.initials: K
authors.lastname: Robeyns
authors.forename: Jean-Bernard
authors.initials: JB
authors.lastname: Behr
mesh_terms: D000818:Animals; D002417:Cattle; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D013379:Substrate Specificity; D005644:alpha-L-Fucosidase / Q000037:antagonists & inhibitors*
chemical_list: D004791:Enzyme Inhibitors; D011759:Pyrrolidines; C415669:codonopsinine; D005644:alpha-L-Fucosidase