title: Aminocyclopentanols as sugar mimics. Synthesis from unsaturated bicyclic lactones by Overman rearrangement.
abstract: Bicyclic cyclopentane lactones, prepared from bromodeoxyaldonolactones, were transformed into aminocyclopentanols with an Overman rearrangement as the key step. Two of the compounds prepared, 7 and 19, were found to be good inhibitors of jack bean alpha-mannosidase and beta-D-N-acetylglucosaminidase, respectively.
authors: Department of Chemistry, Technical University of Denmark, Building 201, DK-2800, Kgs Lyngby, Denmark.
authors: Marie
authors: M
authors: Bøjstrup
authors: Mette
authors: M
authors: Fanefjord
authors: Inge
authors: I
authors: Lundt
mesh_terms: D000118:Acetylglucosaminidase / Q000037:antagonists & inhibitors*; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D007783:Lactones / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D043323:alpha-Mannosidase / Q000037:antagonists & inhibitors*
chemical_list: D003517:Cyclopentanes; D004791:Enzyme Inhibitors; D007783:Lactones; C016327:cyclopentanol; D043323:alpha-Mannosidase; D000118:Acetylglucosaminidase